Composition with stabilized taste and odor (ii)

ABSTRACT

Suggested is a composition with stabilized taste and/or odor, comprising (a) at least one acetophenone derivative of formula (I) wherein R 1  stands for hydrogen or methyl, and R 2  stands for hydrogen, hydroxyl or a —OCH 3  group, or a cosmetically pharmaceutically acceptable salt thereof, and (b) at least one mono- or polyunsaturated C 8 -C 22  fatty acid or its monohydric polyhydric C 1 -C 18  alkyl alcohols ester.

FIELD OF INVENTION

The present invention belongs to the field of cosmetic products and foodproducts and refers to compositions comprising selected acetophenonederivative for stabilizing the taste and/or odor of the contained fattyacids and esters thereof, as well as the personal care products and foodproducts comprising the said compositions with stabilized taste and/orodor.

STATE OF THE ART

Fatty acids (esters) are the main constituents of oils and fats. Theypossess a simple structure consisting of a long hydrocarbonate chainwith about 12-22 carbon atoms and one or more carboxylic (acyl) groups.According to the number of the present double bonds between the carbonatoms fatty acids (esters) are generally divided into saturated,monounsaturated and polyunsaturated fatty acids (esters). At presentmost fatty acids (esters) are obtained from natural origin includingvegetable and animal origin, such as hard animal fats, coconut oil, palmkernel oil and soybean oil. The most common naturally occurring fattyacids are palmitic, stearic, oleic and linoleic acids. With theexception of the tropical oils such as palm and coconut oil, themajority of fatty acids (esters) in most plant- and animal-derived oilsof commercial significance contain eighteen carbon atoms. Other fattyacids (esters) belong to synthetic compounds obtained from petroleum.Thanks to the beneficial physical and biological properties, theapplication of fatty acids (esters) is overwhelming.

Fatty acids (esters) are of great importance in cosmetics industry andbecoming more and more commonly used components in many cosmeticformulations for daily care of the face, body and hair. Naturallyoccurring fatty acids (esters) are components of skin and are componentsof a complex mixture that makes up the outermost layer. Because of theiroiling, softening, smoothing and protective properties, fatty acids(esters) can prevent water loss through the skin, mainly by means ofmaking a protective layer on the epidermis. Additionally they soften thestratum corneum and reduce inflammation of the skin, thereby weakeningthe sensation of pain. However with increasing age the natural synthesisof cutaneous fatty acids (esters) declines, which causes that skinexcessively dehydrates. In order to avoid the unwanted drying of skincaused by the deficiency in fatty acids (esters), in most marketedcosmetic products fatty acids (esters) are applied as an indispensablecosmetic components.

Besides the application in the field of cosmetics, fatty acids (esters)also play a key role in food and nutrition industry, because of theirbiological effects in proper functioning of the human body—in metabolismas major metabolic fuel (storage and transport of energy), as essentialcomponents of all membranes, and as gene regulators. The edible fattyacids (esters) mostly belong to polyunsaturated fatty acids, which arenot metabolically synthesized in mammals and therefore termed as“essential fatty acids”. It has been reported that for human the minimumintake to avoid clinical symptoms of deficiency, taking “ω-3” fattyacids (such as docosahexaenoic acid (DHA) and eicosapentaenoic acid(EPA)) as an example, is approximately 0.5 g per day. In addition it hasbeen proved by many epidemiological and experimental studies that theadditional intake of “essential fatty acids” has significant beneficialeffects. In order to satisfy the huge requirement of consumers on theessential fatty acids (esters) there are increasing number of variousfood and nutritional products in the market, which supply enough amountof the essential fatty acids (esters).

Although the application of fatty acids (esters) in cosmetic productsand food products is mature technology, there are still some unsolvedproblems mainly concerning the complex storage of raw materials and thelimited shelf-life of the end product, which is caused by the rancidityof the contained unsaturated fatty acids (esters). Rancidification isthe process which causes a substance to become rancid, meaning having arank, unpleasant smell or taste. Specifically, it is considered to bethe hydrolysis and/or oxidation of fats into short-chain aldehydes andketones, which are mostly volatile and objectionable in taste and odour.This process results in the rancidity of the fatty acids (esters) andthe end products. It is obvious that oils and fats containing rancidfatty acids (esters) cannot be further processed into corresponding endproducts, and the rancid end products cannot be sold on market or usedby the consumer any more. Both of them lead to the increase ofproduction costs, which is unacceptable both by the manufacturer and theconsumers.

In order to avoid or weaken the rancidity of fatty acids (esters) manymethods have been carried out. For example in industry antioxidants areoften used as preservatives in fat-containing foods or cosmetics todelay the onset or slow the development of rancidity due to oxidation.From the state of the art numerous publications are also known to solvethe rancidity-problem.

The patent application KR 20100105234 reported a composition forpreventing rancidity of unsaturated fatty acids, which comprisespotassium chloride, potassium carbonate, magnesium chloride, calciumlactate and sodium citrate.

The international patent application WO 92/22282 disclosed oilcomponents for cosmetic and/or pharmaceutical preparations. Thispublished oil components consist entirely or mainly of Guerbetcarbonates. Such oil components not only have good compatibility withthe skin and mucous membrane but are also highly stable with respect torancidity.

In the patent application US 2005/0244564 a method is described toincrease the oxidative stability of oil-containing food products. Basedon the discovery that higher level of oleic acid and lower level oflinoleic acid contribute to improving the oxidative stability, thedisclosed method is characterized by the addition of an oil rich in ω-3fatty acid to a product with large ratio between oleic acid and linoleicacid.

The subject matter of patent application GB 813, 538 A refers to the useof 5-acenaphthenol as an antioxidant for eliminating the deleteriouseffects of oxidation and improving the stability of oxidizablecompositions including solid fats, fatty oils and so on.

U.S. Pat. No. 2,521,856 A provided a new mixture comprising (a)butylated hydroquinone monoalkyl ether wherein the alkyl group containsfrom 1 to 4 carbon atoms inclusive; (b) hydroquinione and (c) an acidicmaterial selected from the group consisting of citric acid, ascorbicacid, oxalic acid, phosphoric acid, ethyl acid phosphate and triethylphosphate to improve the stabilization of materials normally subject tooxidative rancidity due to their content of glycerides of fatty acids.

In the patent application GB 595838 A stabilised edible vegetable,animal, fish oil, fats and waxes are provided, wherein the mentionededible materials were brought into contact with a small portion ofthio-di-saturated fatty acid, or ester, amide, salt, or anhydridethereof.

GB 618409 A disclosed nordihydroguaiaretic acid of vegetable origin asantioxidant to preserve lard, butter, edible oils and the like in afresh and edible condition for long periods so as to permit packaging insealed containers and storage in hot climatic conditions for longperiods.

Although, there are already several fatty acids (esters) containingcompositions reported with good stability with respect to rancidity,most of them are based on increasing the ratio of saturated fatty acidsin the obtained composition. However the rate of saturated tounsaturated fatty acids is very important for human nutrition. Thatmeans high levels of saturated fatty acids are on the one hand desirableto increase stability of fatty acids (esters), while on the other handundesirable e.g. nutritionally, because high levels of saturated fattyacids are frequently considered do have influence by increasing theconcentration of low density lipoproteins (LDL), affecting the ratio ofLDL to HDL (high density lipoproteins), promoting clotting and vascularsmooth muscle proliferation.

Therefore there is a significant need to find a novel fatty acids(esters)-containing composition with stabilized taste and/or odor aswell as improved resistance to oxidation and rancidity. With theutilization of the fatty acids (esters)-containing composition, a moreeffective storage of fatty acids (esters) as raw materials and longershelf-life of the end product comprising fatty acids (esters) would berealized, without intentionally decreasing the level of unsaturatedfatty acids (esters). The new composition shall maintain all theexcellent physical and biological properties of the contained fattyacids (esters) and further possess excellent resistance to rancidity.Preferably the used stabilizing agent contained in the compositionshould be of defined chemical structure and purity, toxicologically safein use, well tolerated, effective already at low concentrations, easy toformulate, colorless and odorless.

Based on the known important benefit of fatty acids (esters)-containingcomposition with stabilized taste and/or odor in the cosmetic and foodindustry, the main problem underlying the present invention has beenproviding a new composition comprising fatty acids (esters), wherein theunsaturated fatty acids (esters) contained still express their originalphysical and biological properties and are well protected from oxidationand rancidity. Another problem solved by the present invention has beenproviding a new method to preserve unsaturated fatty acids (esters) fromoxidation and rancidity. Besides a further problem underlying thepresent invention has been supplying cosmetic and food products withbetter resistance to rancidity and longer shelf-life.

DESCRIPTION OF THE INVENTION

Object of the present invention is a composition with stabilized tasteand/or odor comprising

-   -   (a) at least one acetophenone derivative of formula (I)

-   -   wherein    -   R₁ stands for hydrogen or methyl, and    -   R₂ stands for hydrogen, hydroxyl or a —OCH₃ group, or a        cosmetically or pharmaceutically acceptable salt thereof,

and

-   -   (b) at least one mono- or polyunsaturated C₈-C₂₂ fatty acid or        its monohydric or polyhydric C₁-C₁₈ aliphatic alcohols ester

The amount of acetophenone derivative of formula (I) in the compositionsaccording to the present invention is in the range from about 0.01 to 5wt. %, preferably in the range from 0.05 to 2 wt. %, and particularlypreferably in the range from 0.1 to 1 wt. % relative to the total weightof the composition.

It has been surprisingly observed that, though acetophenone derivativesof formula (I) as a known antioxidant has much weaker antioxidantactivity to the conventional antioxidants such as alpha-tocopherol, evenat a low concentration acetophenone derivatives of formula (I) shows asuperior activity to preserve various mono- or polyunsaturated C₈-C₂₂fatty acids and esters thereof from rancidity than other antioxidants.

Acetophenone Derivatives

Acetophenone derivatives according to the present invention representknown compounds that can be obtained by ordinary methods of organicchemistry. It is understood that both substituents OR₁ and R₂ can belocated in ortho, meta or para position towards the methylketo group.

Preferably, the species are selected from the group consisting of

or their mixtures. In as far the definition refers to cosmetically orpharmaceutically acceptable salts of said derivatives, this means thatthese salts can be safely used for pharmaceutical purposes. This doesnot mean that the present invention or any aspect thereof is restrictedto the use of a compound of formula (I) or a corresponding mixture forpharmaceutical purposes. Generally, if a salt can be used forpharmaceutical purposes it can likewise be used for cosmetic purposes,or in food or beverage formulations. In particular, the sodium andpotassium and ammonium salts of compounds of formula (I) are consideredas (pharmaceutically) acceptable salts. In some cases the utilization ofthe respective ionic compound or solvate carrier proves to be superiorto the unmodified derivative. The (pharmaceutically) acceptable salts(and the corresponding solvates) of compounds of formula (I) can beprepared by standard procedures. Hereinafter, any reference to acompound of formula (I) or a corresponding mixture as defined above isto be understood as comprising an additional reference to corresponding(pharmaceutically) acceptable salts thereof.

In a preferred embodiment the composition comprise or contain two orthree of the compounds (Ia), (Ib) and (Ic), as for example2-hydroxyacetophenone and 3-hydroxyacetophenone, or2-hydroxyacetophenone and 4-hydroxyacetophenone, or3-hydroxyacetophenone and 4-hydroxyacetophenone

In a most preferred embodiment the composition of the present inventioncomprise 4-hydroxyacetophenone.

Unsaturated Fatty Aid and Ester Thereof

Unsaturated fatty acid and ester thereof as component (b) according tothe present invention refer to mono- or polyunsaturated C₈-C₂₂ fattyacid and its monohydric or polyhydric C₁-C₁₈ aliphatic alcohols ester.

Preferably the component (b) of the composition according to the presentinvention comprises:

(b-1) at least one acyl compound of formula (II)

-   -   wherein    -   R stands for hydrogen atom or a C₁-C₁₈ alkyl group and    -   X represents a mono- or polyunsaturated C₈-C₂₂ acyl group,

and/or

(b-2) at least one acylglycerol compound of formula (III)

-   -   wherein    -   X′, X″ and X″′ independently of one another represents a        hydrogen atom or a saturated or mono- or polyunsaturated C₈-C₂₂        acyl group,    -   with the proviso that X′, X″ and X″′ do not simultaneously        represent hydrogen atom and at least one of X′, X″ and X′″ being        unsaturated acyl group.

Acyl Compound

According to the present invention the acyl compound of formula (II) ascomponent (b-1) includes mono- or polyunsaturated C₈-C₂₂ fatty acids andtheir esters of C₁-C₁₈ alcohols.

The typical representatives of component (b-1) comprise but not limitedto palmitioleic acid (C16: 1), oleic acid (C18: 1), elaidic acid (C18:1), ricinoleic acid (C18: 1), petroselinic acid (C18: 1), vaccenic acid(C18: 1), linoleic acid (C18: 2), α-linolenic acid (C18: 3), γ-linolenicacid (C18: 3), cis-linolenic acid (C18: 3), punicic acid (C18: 3),oleostearynic acid (C18: 3), stearidonic acid (C18:4), gondoci acid(C20: 1), gadoleic acid (C20: 1), paullinic acid (C20: 1), arachidonicacid (C20: 4), erucic acid (C22: 1), EPA (C20: 5), docosapentaenoic acid(C20: 5), DHA (C22: 6), myristyl oleate, myristyl erucate, cetyl oleate,cetyl erucate, stearyl oleate, stearyl erucate, isostearyl oleate, oleylmyristate, oleyl palmitate, oleyl stearate, oleyl isostearate, oleyloleate, oleyl behenate, oleyl erucate, behenyl oleate, behenyl erucate,erucyl myristate, erucyl palmitate, erucyl stearate, erucyl isostearate,erucyl oleate, erucyl behenate and erucyl erucate.

In a preferred embodiment of the present invention in acyl compound offormula (II) R is hydrogen atom and X is a mono-or polyunsaturatedC₁₆-C₂₂ acyl group.

In a most preferred embodiment of the present invention the component(b-1) is oleic acid, linoleic acid, γ-linolenic acid, α-linolenic acid,EPA and DHA.

Linoleic acid occurs most abundantly in sunflower oil, soybean oil,safflower, corn oil, sesame oil, peanut oil, grape seed oil and wheatgerm oil. It is essential to the skin's barrier function. In dry skin itstrengthens the lipid barrier of epidermis, protects againsttransepidermal loss of water and normalizes the skin metabolism. Inpersons with acne skin, a decrease in linoleic acid content in sebum isobserved, which leads to blocked pores and formation of comedos andeczemas. The use of linoleic acid for oily skin and problematic skincare leads to improvement of the work of sebaceous glands, unblocking ofpores and decrease in the number of comedos.

┌-linolenic acid belongs to omega-6 series and can be obtained fromnatural sources including borage oil, black currant oil, eveningprimrose oil and hemp oil. Besides α-linolenic acid is a representativeof omega-3 group and is found in linseed oil, soybean oil, rapeseed oil,wheat germ oil, walnut oil, and algae and marine phytoplankton. Both α-and γ-linolenic acids are physiological components of cell membranes ormitochondria membranes in human cells.

Polyunsaturated fatty acids such as eicosapentaenoic acid (EPA) ordocosahexaenoic acid (DHA) are found in fish oil from salmon, cod,herring, mackerel and are metabolites of algae and marine phytoplankton.

Acylglycerol Compound

Acylglycerol compounds of formula (III) as component (b-2) of thecomposition according to the present invention concern mono-, di-, ortriglycerides formed from glycerol and C₈-C₂₂ fatty acids, wherein thefatty acids comprise but not limited to caprylic acid (C8: 0), decanoicacid (C10: 0), lauric acid (C12: 0), myristate acid (C14: 0), palmiticacid (C16: 0), palmitioleic acid (C16: 1), margaric acid (C17: 0),stearic acid (C18: 0), oleic acid (C18: 1), elaidic acid (C18: 1),ricinoleic acid (C18: 1), petroselinic acid (C18: 1), vaccenic acid(C18: 1), linoleic acid (C18: 2), α-linolenic acid (C18: 3), γ-linolenicacid (C18: 3), cis-linolenic acid (C18: 3), punicic acid (C18: 3),oleostearynic acid (C18: 3), stearidonic acid (C18:4), arachidic acid(C20: 0), gondoci acid (C20: 1), gadoleic acid (C20: 1), paullinic acid(C20: 1), arachidonic acid (C20: 4), erucic acid (C22: 1), EPA (C20: 5),docosapentaenoic acid (C20: 5), docosanoic acid (C22: 0), DHA (C22: 6).

The typical representatives of component (b-2) comprise but not limitedto tri-, di- or monoglyceryl esters of palmitoleic acid, oleic acid,linoleic acid, linolenic acid, stearidonic acid, eicosapentaenoic acid,docosahexaenoic acid such as e.g. triolein, trilinolein, trilinolenin,1,3-diolein, 1,2-diolein, 1,3-dilinolein, 1,2-dilinolein,1,3-dilinolenin, 1,2-dilinolenin, 1-monoolein, 2-monoolein,1-monolinolein, 2-monolinolein, 1-monolinolenin, 2-monolinolenin andmixed di- or triglyceryl esters such as e.g.glyceryl-1-stearate-3-oleate, glyceryl-1-stearate-2-oleate,glyceryl-2-stearate-1-oleate, glyceryl-1-stearate-3-linoleate,glyceryl-1-stearate-2-linoleate, glyceryl-2-stearate-1-linoleate,glyceryl-1-stearate-3-linolenate, glyceryl-1-stearate-2-linolenate,glyceryl-2-stearate-1-linolenate, glyceryl-1-palmitate-3-oleate,glyceryl-1-palmitate-2-oleate, glyceryl-2-palmitate-1-oleate,glyceryl-1-palmitate-3-linoleate, glyceryl-1-palmitate-2-linoleate,glyceryl-2-palmitate-1-linoleate, glyceryl-1-palmitate-3-linolenate,glyceryl-1-palmitate-2-linolenate, glyceryl-2-palmitate-1-linolenate,glyceryl-1,2-distearate-3-oleate, glyceryl-1,3-distearate-2-oleate,glyceryl-2,3-distearate-1-oleate, glyceryl-1,2-distearate-3-linoleate,glyceryl-1,3-distearate-2-linoleate,glyceryl-2,3-distearate-1-linoleate,glyceryl-1,2-distearate-3-linolenate,glyceryl-1,3-distearate-2-linolenate,glyceryl-2,3-distearate-1-linolenate,glyceryl-1,2-dipaInnitate-3-oleate, glyceryl-1,3-dipalmitate-2-oleate,glyceryl-2,3-dipalmitate-1-oleate, glyceryl-1,2-dipalmitate-3-linoleate,glyceryl-1,3-dipalmitate-2-linoleate,glyceryl-2,3-dipalmitate-1-linoleate,glyceryl-1,2-dipalmitate-3-linolenate,glyceryl-1,3-dipalmitate-2-linolenate,glyceryl-2,3-dipalmitate-1-linolenate, glyceryl-1,2-dioleate-3-stearate,glyceryl-1,3-dioleate-2-stearate, glyceryl-1,2-dilinoleate-3-stearate,glyceryl-1,3-dilinoleate-2-stearate,glyceryl-1,2-dilinolenate-3-stearate,glyceryl-1,3-dilinolenate-2-stearate, glyceryl-1,2-dioleate-3-palmitate,glyceryl-1,3-dioleate-2-palmitate, glyceryl-1,2-dilinoleate-3-palmitate,glyceryl-1,3-dilinoleate-2-palmitate,glyceryl-1,2-dilinolenate-3-palmitate,glyceryl-1,3-dilinolenate-2-palmitate.

In a preferred embodiment of the present invention the acylglycerolcompound of formula (III) is a mono-, di-, or triglyceride origined fromvegetable oils.

In another preferred embodiment of the present invention theacylglycerol compound of formula (III) is a diglyceride, which mainlyorigin from vegetable oils, i.e. two of X′, X″ and X′″ of formula (III)independently of one another represents a saturated or mono- orpolyunsaturated C₈-C₂₂ acyl group with the proviso that one of them isunsaturated.

In another preferred embodiment of the present invention theacylglycerol compound of formula (III) is a monoglyceride, which mainlyorigin from vegetable oils, i.e. one of X′, X″ and X′″ of formula (III)independently of one another represents a mono- or polyunsaturatedC₈-C₂₂ acyl group.

Vegetable oils are liquid vegetable fats that remain in the liquid format room temperature. These lipids are most commonly extracted fromvarious parts of plants such as seeds, fruits, or plant seedlings. Underthe chemical terms they are a combination of triglycerides of highersaturated and unsaturated fatty acids. In other words, these compoundsare esters of glycerol and higher fatty acids, containing in theirstructure long aliphatic carbon chains. According to the presentinvention the vegetable oils comprise but not limited to Argan oil,Chokeberry (seed) oil, Avocado oil, Peach (pits) oil, Canola oil,Nigella oil, Pumpkin (pumpkin seed) oil, Wild rose (seeds) oil,Pomegranate seeds oil, Jojoba (liquid wax) oil, Cocoa/cocoa butter,Wheat sprout oil, Coconut/coconut butter, Safflower oil, Corn oil,Camelina oil, Flax seed oil, Macadamia oil, Raspberries seeds oil,Meadowfoam seeds oil, Passiflora seeds oil, Almond oil, Neem oil,Moringa oil, Borago oil, Olive oil, Peanuts oil, Hazelnuts oil, Walnutoil, Palm oil, Papaya seeds oil, Parsley seeds oil, Seabuckthorn oil,Castor oil, Rice oil, Sesame oil, Shea butter/karité butter, Sunfloweroil, Soybean oil, Tamanu oil, Evening primrose oil, Grape seeds oil,Cranberry seeds oil.

In a most preferred embodiment of the present invention the component(b-2) of formula (III) is composed mainly of oleic, linoleic, andlinolenic esterified on a glycerol molecule in various combinations.

Besides the present invention claims the use of acetophenone derivativeof formula (I)

-   -   wherein    -   R₁ stands for hydrogen or methyl, and    -   R₂ stands for hydrogen, hydroxyl or a —OCH₃ group, or a        cosmetically or pharmaceutically acceptable salt thereof,    -   for stabilizing the taste and/or odor of unsaturated fatty acid        (esters).

Preferably, the acetophenone derivative of formula (I) are selected fromthe group consisting of

or their mixtures. More preferably the acetophenone derivative offormula (I) is 4-hydroxyacetophenone.

In a preferred embodiment the unsaturated fatty acids (esters) are mono-or polyunsaturated C₈-C₂₂ fatty acids or its monohydric or polyhydricC₁-C₁₈ aliphatic alcohols ester.

In a more preferred embodiment the mono- or polyunsaturated C₈-C₂₂ fattyacids or its monohydric or polyhydric C₁-C₁₈ aliphatic alcohols estercomprise:

(b-1) at least one acyl compound of formula (II)

-   -   wherein    -   R stands for hydrogen atom or an C₁-C₁₈ alkyl group and    -   X represents a mono- or polyunsaturated C₈-C₂₂ acyl group,        and/or

(b-2) at least one acylglycerol compound of formula (III)

-   -   wherein    -   X′, X″ and X″′ independently of one another represents a        hydrogen atom or a saturated or mono- or polyunsaturated C₈-C₂₂        acyl group,    -   with the proviso that X′, X″ and X″′ do not simultaneously        represent hydrogen atom and at least one of X′, X″ and X′″ being        unsaturated acyl group.

In another preferred embodiment the used amount of acetophenonederivative of formula (I) is 0.01 to 5 wt. %, preferably in the rangefrom 0.05 to 2 wt. %, and particularly preferably in the range from 0.1to 1 wt. % relative to the total weight of the composition.

INDUSTRIAL APPLICATION

Personal Care Compositions

Another object of the present invention is to provide a personal carecomposition or a cosmetic composition, which comprise the compositionwith stabilized taste and/or odor according to the present invention.

The personal care or cosmetic compositions may contain abrasives,antiacne agents, agents against ageing of the skin, anticellulitisagents, antidandruff agents, antiinflammatory agents,irritation-preventing agents, irritation-inhibiting agents,antioxidants, astringents, perspiration-inhibiting agents, antisepticagents, antistatics, binders, buffers, carrier materials, chelatingagents, cell stimulants, cleansing agents, care agents, depilatoryagents, surface-active substances, deodorizing agents, antiperspirants,softeners, emulsifiers, enzymes, essential oils, fibres, film-formingagents, fixatives, foam-forming agents, foam stabilizers, substances forpreventing foaming, foam boosters, gelling agents, gel-forming agents,hair care agents, hair-setting agents, hair-straightening agents,moisture-donating agents, moisturizing substances, moisture-retainingsubstances, bleaching agents, strengthening agents, stain-removingagents, optically brightening agents, impregnating agents,dirt-repellent agents, friction-reducing agents, lubricants,moisturizing creams, ointments, opacifying agents, plasticizing agents,covering agents, polish, gloss agents, polymers, powders, proteins,re-oiling agents, abrading agents, silicones, skin-soothing agents,skin-cleansing agents, skin care agents, skin-healing agents,skin-lightening agents, skin-protecting agents, skin-softening agents,cooling agents, skin-cooling agents, warming agents, skin-warmingagents, stabilizers, UV-absorbing agents, UV filters, detergents, fabricconditioning agents, suspending agents, skin-tanning agents, thickeners,vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono-or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy-fattyacids, liquefiers, dyestuffs, colour-protecting agents, pigments,anticorrosives, aromas, flavouring substances, odoriferous substances,polyols, surfactants, electrolytes, organic solvents or siliconederivativesand the like as additional auxiliaries and additives.

Surfactants

Other preferred auxiliaries and additives are anionic and/or amphotericor zwitterionic surfactants. Typical examples of anionic surfactants aresoaps, alkyl benzenesulfonates, alkanesulfonates, olefin sulfonates,alkylether sulfonates, glycerol ether sulfonates, methyl estersulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ethersulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxymixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide(ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylicacids and salts thereof, fatty acid isethionates, fatty acidsarcosinates, fatty acid taurides, N-acylamino acids such as, forexample, acyl lactylates, acyl tartrates, acyl glutamates and acylaspartates, alkyl oligoglucoside sulfates, protein fatty acidcondensates (particularly wheat-based vegetable products) and alkyl(ether) phosphates. If the anionic surfactants contain polyglycol etherchains, they may have a conventional homolog distribution although theypreferably have a narrow-range homolog distribution. Typical examples ofamphoteric or zwitterionic surfactants are alkylbetaines,alkylamidobetaines, aminopropionates, aminoglycinates, imidazoliniumbetaines and sulfobetaines. The surfactants mentioned are all knowncompounds. Information on their structure and production can be found inrelevant synoptic works, cf. for example J. Falbe (ed.), “Surfactants inConsumer Products”, Springer Verlag, Berlin, 1987, pages 54 to 124 or J.Falbe (ed.), “Katalysatoren, Tenside and Mineralöladditive (Catalysts,Surfactants and Mineral Oil Additives)”, Thieme Verlag, Stuttgart, 1978,pages 123-217. The percentage content of surfactants in the preparationsmay be from 0.1 to 10% by weight and is preferably from 0.5 to 5% byweight, based on the preparation.

Oil Bodies

Suitable oil bodies, which form constituents of the O/W emulsions, are,for example, Guerbet alcohols based on fatty alcohols having 6 to 18,preferably 8 to 10, carbon atoms, esters of linear saturatedC6-C22-fatty acids with linear or branched C6-C22-fatty alcohols oresters of branched saturated C6-C13-carboxylic acids with linear orbranched C6-C 22-fatty alcohols, such as, for example, myristylmyristate, myristyl palmitate, myristyl stearate, myristyl isostearate,myristyl behenate, cetyl myristate, cetyl palmitate, cetyl stearate,cetyl isostearate, cetyl behenate, stearyl myristate, stearyl palmitate,stearyl stearate, stearyl isostearate, stearyl behenate, isostearylmyristate, isostearyl palmitate, isostearyl stearate, isostearylisostearate, isostearyl behenate, oleyl myristate, oleyl palmitate,oleyl stearate, oleyl isostearate, oleyl behenate, behenyl myristate,be-henyl palmitate, behenyl stearate, behenyl isostearate, behenylbehenate, erucyl myristate, erucyl palmitate, erucyl stearate, erucylisostearate, erucyl behenate and. Also suitable are esters of saturatedlinear C6-C22-fatty acids with branched alcohols, in particular2-ethylhexanol, esters of C18-C38-alkylhydroxy carboxylic acids withlinear or branched C6-C 22-fatty alcohols, in particular Dioctyl Malate,esters of linear and/or branched fatty acids with polyhydric alcohols(such as, for example, propylene glycol, dimerdiol or trimertriol)and/or Guerbet alcohols, triglycerides based on saturated C6-C10-fattyacids, liquid mono-/di-/triglyceride mixtures based on saturatedC6-C18-fatty acids, esters of C6- C22-fatty alcohols and/or Guerbetalcohols with aromatic carboxylic acids, in particular benzoic acid,esters of C2-C12-dicarboxylic acids with linear or branched alco-holshaving 1 to 22 carbon atoms or polyols having 2 to 10 carbon atoms and 2to 6 hydroxyl groups, branched primary alcohols, substitutedcyclohexanes, linear and branched C6-C22-fatty alcohol carbonates, suchas, for example, Dicaprylyl Carbonate (Cetiol® CC), Guerbet carbonates,based on fatty alcohols having 6 to 18, preferably 8 to 10, carbonatoms, esters of benzoic acid with linear and/or branchedC6-C22-alcohols (e.g. Finsolv® TN), linear or branched, symmetrical orasymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group,such as, for example, dicaprylyl ether (Cetiol® OE), ring-openingproducts of epoxidized fatty acid esters with polyols, silicone oils(cyclomethicones, silicone methicone grades, etc.) and/or aliphatic ornaphthenic hydrocarbons, such as, for example, squalane, squalene ordialkylcyclohexanes.

Emulsifiers

Other surfactants may also be added to the preparations as emulsifiers,including for example:

-   -   products of the addition of 2 to 30 mol ethylene oxide and/or 0        to 5 mol propylene oxide onto linear C₈₋₂₂ fatty alcohols, onto        C₁₂₋₂₂ fatty acids and onto alkyl phenols containing 8 to 15        carbon atoms in the alkyl group;    -   C_(12/18) fatty acid monoesters and diesters of addition        products of 1 to 30 mol ethylene oxide onto glycerol;    -   glycerol mono- and diesters and sorbitan mono- and diesters of        saturated and unsaturated fatty acids containing 6 to 22 carbon        atoms and ethylene oxide addition products thereof;    -   addition products of 15 to 60 mol ethylene oxide onto castor oil        and/or hydrogenated castor oil;    -   polyol esters and, in particular, polyglycerol esters such as,        for example, polyglycerol polyricinoleate, polyglycerol        poly-12-hydroxystearate or polyglycerol dimerate isostearate.        Mixtures of compounds from several of these classes are also        suitable;    -   addition products of 2 to 15 mol ethylene oxide onto castor oil        and/or hydrogenated castor oil;    -   partial esters based on linear, branched, unsaturated or        saturated C_(6/22) fatty acids, ricinoleic acid and        12-hydroxystearic acid and glycerol, polyglycerol,        pentaerythritol, -dipentaerythritol, sugar alcohols (for example        sorbitol), alkyl glucosides (for example methyl glucoside, butyl        glucoside, lauryl glucoside) and polyglucosides (for example        cellulose);    -   mono-, di and trialkyl phosphates and mono-, di- and/or        tri-PEG-alkyl phosphates and salts thereof;    -   wool wax alcohols;    -   polysiloxane/polyalkyl polyether copolymers and corresponding        derivatives;    -   mixed esters of pentaerythritol, fatty acids, citric acid and        fatty alcohol and/or mixed esters of C₆₋₂₂ fatty acids, methyl        glucose and polyols, preferably glycerol or polyglycerol,    -   polyalkylene glycols and    -   glycerol carbonate.

The addition products of ethylene oxide and/or propylene oxide ontofatty alcohols, fatty acids, alkylphenols, glycerol mono- and diestersand sorbitan mono- and diesters of fatty acids or onto castor oil areknown commercially available products. They are homologue mixtures ofwhich the average degree of alkoxylation corresponds to the ratiobetween the quantities of ethylene oxide and/or propylene oxide andsubstrate with which the addition reaction is carried out. ₀₁₂₁₁₈ fattyacid monoesters and diesters of addition products of ethylene oxide ontoglycerol are known as lipid layer enhancers for cosmetic formulations.The preferred emulsifiers are described in more detail as follows:

Partial glycerides. Typical examples of suitable partial glycerides arehydroxystearic acid monoglyceride, hydroxystearic acid diglyceride,isostearic acid monoglyceride, isostearic acid diglyceride, oleic acidmonoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride,ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic aciddiglyceride, linolenic acid monoglyceride, linolenic acid diglyceride,erucic acid monoglyceride, erucic acid diglyceride, tartaric acidmonoglyceride, tartaric acid diglyceride, citric acid monoglyceride,citric acid diglyceride, malic acid monoglyceride, malic aciddiglyceride and technical mixtures thereof which may still contain smallquantities of triglyceride from the production process. Additionproducts of 1 to 30 and preferably 5 to 10 mol ethylene oxide onto thepartial glycerides mentioned are also suitable.

Sorbitan esters. Suitable sorbitan esters are sorbitan monoisostearate,sorbitan sesquiisostearate, sorbitan diisostearate, sorbitantriisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitandioleate, sorbitan trioleate, sorbitan monoerucate, sorbitansesquierucate, sorbitan dierucate, sorbitan trierucate, sorbitanmonoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate,sorbitan triricinoleate, sorbitan monohydroxystearate, sorbitansesquihydroxystearate, sorbitan dihydroxystearate, sorbitantrihydroxystearate, sorbitan monotartrate, sorbitan sesquitartrate,sorbitan ditartrate, sorbitan tritartrate, sorbitan monocitrate,sorbitan sesquicitrate, sorbitan dicitrate, sorbitan tricitrate,sorbitan monomaleate, sorbitan sesquimaleate, sorbitan dimaleate,sorbitan trimaleate and technical mixtures thereof. Addition products of1 to 30 and preferably 5 to 10 mol ethylene oxide onto the sorbitanesters mentioned are also suitable.

Polyglycerol esters. Typical examples of suitable polyglycerol estersare Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls® PGPH),Polyglycerin-3-Diisostearate (Lameform® TGI), Polyglyceryl-4 Isostearate(Isolan® GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose Distearate(Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether(Chimexane® NL), Polyglyceryl-3 Distearate (Cremophor® GS 32) andPolyglyceryl Polyricinoleate (Admul® WOL 1403), Polyglyceryl DimerateIsostearate and mixtures thereof. Examples of other suitablepolyolesters are the mono-, di- and triesters of trimethylol propane orpentaerythritol with lauric acid, cocofatty acid, tallow fatty acid,palmitic acid, stearic acid, oleic acid, behenic acid and the likeoptionally reacted with 1 to 30 mol ethylene oxide.

Anionic emulsifiers. Typical anionic emulsifiers are aliphatic C₁₂₋₂₂fatty acids, such as palmitic acid, stearic acid or behenic acid forexample, and C₁₂₋₂₂ dicarboxylic acids, such as azelaic acid or sebacicacid for example.

Amphoteric emulsifiers. Other suitable emulsifiers are amphboteric orzwitterionic surfactants. Zwitterionic surfactants are surface-activecompounds which contain at least one quaternary ammonium group and atleast one carboxylate and one sulfonate group in the molecule.Particularly suitable zwitterionic surfactants are the so-calledbetaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, forexample cocoalkyl dimethyl ammonium glycinate,N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for examplecocoacylaminopropyl dimethyl ammonium glycinate, and2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18carbon atoms in the alkyl or acyl group and cocoacylaminoethylhydroxyethyl carboxymethyl glycinate. The fatty acid amide derivativeknown under the CTFA name of Cocamidopropyl Betaine is particularlypreferred. Ampholytic surfactants are also suitable emulsifiers.Ampholytic surfactants are surface-active compounds which, in additionto a C_(8/18) alkyl or acyl group, contain at least one free amino groupand at least one —COOH— or —SO₃H— group in the molecule and which arecapable of forming inner salts. Examples of suitable ampholyticsurfactants are N-alkyl glycines, N-alkyl propionic acids,N-alkylaminobutyric acids, N-alkyliminodipropionic acids,N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acidscontaining around 8 to 18 carbon atoms in the alkyl group. Particularlypreferred ampholytic surfactants are N-cocoalkylaminopropionate,cocoacylaminoethyl aminopropionate and C_(12/18) acyl sarcosine.

Superfatting Agents and Consistency Factors

Superfatting agents may be selected from such substances as, forexample, lanolin and lecithin and also polyethoxylated or acylatedlanolin and lecithin derivatives, polyol fatty acid esters,monoglycerides and fatty acid alkanolamides, the fatty acidalkanolamides also serving as foam stabilizers.

The consistency factors mainly used are fatty alcohols or hydroxyfattyalcohols containing 12 to 22 and preferably 16 to 18 carbon atoms andalso partial glycerides, fatty acids or hydroxyfatty acids. Acombination of these substances with alkyl oligoglucosides and/or fattyacid N-methyl glucamides of the same chain length and/or polyglycerolpoly-12-hydroxystearates is preferably used.

Thickening Agents and Rheology Additives

Suitable thickeners are polymeric thickeners, such as Aerosil® types(hydrophilic silicas), polysaccharides, more especially xanthan gum,guar-guar, agar-agar, alginates and tyloses, carboxymethyl cellulose andhydroxyethyl cellulose, also relatively high molecular weightpolyethylene glycol monoesters and diesters of fatty acids,polyacrylates (for example Carbopols® [Goodrich] or Synthalens®[Sigma]), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone,surfactants such as, for example, ethoxylated fatty acid glycerides,esters of fatty acids with polyols, for example pentaerythritol ortrimethylol propane, narrow-range fatty alcohol ethoxylates andelectrolytes, such as sodium chloride and ammonium chloride.

Polymers

Suitable cationic polymers are, for example, cationic cellulosederivatives such as, for example, the quaternized hydroxyethyl celluloseobtainable from Amerchol under the name of Polymer JR 400®, cationicstarch, copolymers of diallyl ammonium salts and acrylamides,quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, forexample, Luviquat® (BASF), condensation products of polyglycols andamines, quaternized collagen polypeptides such as, for example,Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat® L, Grünau),quaternized wheat polypeptides, polyethyleneimine, cationic siliconepolymers such as, for example, amodimethicone, copolymers of adipic acidand dimethylaminohydroxypropyl diethylenetriamine (Cartaretine®,Sandoz), copolymers of acrylic acid with dimethyl diallyl ammoniumchloride (Merquat® 550, Chemviron), polyaminopolyamides and crosslinkedwater-soluble polymers thereof, cationic chitin derivatives such as, forexample, quaternized chitosan, optionally in microcrystallinedistribution, condensation products of dihaloalkyls, for exampledibromobutane, with bis-dialkylamines, for examplebis-dimethylamino-1,3-propane, cationic guar gum such as, for example,Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 of Celanese, quaternizedammonium salt polymers such as, for example, Mirapol® A-15, Mirapol®AD-1, Mirapol® AZ-1 of Miranol and the various polyquaternium types (forexample 6, 7, 32 or 37) which can be found in the market under thetradenames Rheocare® CC or Ultragel® 300.

Suitable anionic, zwitterionic, amphoteric and nonionic polymers are,for example, vinyl acetate/crotonic acid copolymers, vinylpyrrolidone/vinyl acrylate copolymers, vinyl acetate/butylmaleate/isobornyl acrylate copolymers, methyl vinylether/maleicanhydride copolymers and esters thereof, uncrosslinked andpolyol-crosslinked polyacrylic acids, acrylamidopropyl trimethylammoniumchloride/acrylate copolymers, octylacrylamide/methylmethacrylate/tert.-butylaminoethyl nnethacrylate/2-hydroxypropylmethacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinylacetate copolymers, vinyl pyrrolidone/dimethylaminoethylmethacrylate/vinyl caprolactam terpolymers and optionally derivatizedcellulose ethers and silicones.

Pearlising Waxes

Suitable pearlising waxes are, for example, alkylene glycol esters,especially ethylene glycol distearate; fatty acid alkanolamides,especially cocofatty acid diethanolamide; partial glycerides, especiallystearic acid monoglyceride; esters of polybasic, optionallyhydroxy-substituted carboxylic acids with fatty alcohols containing 6 to22 carbon atoms, especially long-chain esters of tartaric acid; fattycompounds, such as for example fatty alcohols, fatty ketones, fattyaldehydes, fatty ethers and fatty carbonates which contain in all atleast 24 carbon atoms, especially laurone and distearylether; fattyacids, such as stearic acid, hydroxystearic acid or behenic acid, ringopening products of olefin epoxides containing 12 to 22 carbon atomswith fatty alcohols containing 12 to 22 carbon atoms and/or polyolscontaining 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixturesthereof.

Silicones

Suitable silicone compounds are, for example, dimethyl polysiloxanes,methylphenyl polysiloxanes, cyclic silicones and amino-, fatty acid-,alcohol-, polyether-, epoxy-, fluorine-, glycoside- and/oralkyl-modified silicone compounds which may be both liquid andresin-like at room temperature. Other suitable silicone compounds aresimethicones which are mixtures of dimethicones with an average chainlength of 200 to 300 dimethylsiloxane units and hydrogenated silicates.A detailed overview of suitable volatile silicones can be found in Toddet al. in Cosm. Toil. 91, 27 (1976).

Waxes and Stabilizers

Besides natural oils used, waxes may also be present in thepreparations, more especially natural waxes such as, for example,candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax,guaruma wax, rice oil wax, sugar cane wax, ouricury wax, montan wax,beeswax, shellac wax, spermaceti, lanolin (wool wax), uropygial fat,ceresine, ozocerite (earth wax), petrolatum, paraffin waxes andmicrowaxes; chemically modified waxes (hard waxes) such as, for example,montan ester waxes, sasol waxes, hydrogenated jojoba waxes and syntheticwaxes such as, for example, polyalkylene waxes and polyethylene glycolwaxes.

Metal salts of fatty acids such as, for example, magnesium, aluminiumand/or zinc stearate or ricinoleate may be used as stabilizers.

Primary Sun Protection Factors

Primary sun protection factors in the context of the invention are, forexample, organic substances (light filters) which are liquid orcrystalline at room temperature and which are capable of absorbingultraviolet radiation and of releasing the energy absorbed in the formof longer-wave radiation, for example heat.

The formulations according to the invention advantageously contain atleast one UV-A filter and/or at least one UV-B filter and/or a broadbandfilter and/or at least one inorganic pigment. Formulations according tothe invention preferably contain at least one UV-B filter or a broadbandfilter, more particularly preferably at least one UV-A filter and atleast one UV-B filter.

Preferred cosmetic compositions, preferably topical formulationsaccording to the present invention comprise one, two, three or more sunprotection factors selected from the group consistiung of 4-aminobenzoicacid and derivatives, salicylic acid derivatives, benzophenonederivatives, dibenzoylmethane derivatives, diphenyl acrylates,3-imidazol-4-yl acrylic acid and esters thereof, benzofuran derivatives,benzylidene malonate derivatives, polymeric UV absorbers containing oneor more organosilicon radicals, cinnamic acid derivatives, camphorderivatives, trianilino-s-triazine derivatives,2-hydroxyphenylbenzotriazole derivatives, phenylbenzimidazole sulfonicacid derivatives and salts thereof, anthranilic acid menthyl esters,benzotriazole derivativesand indole derivatives.

In addition, it is advantageous to combine compounds of formula (I) withactive ingredients which penetrate into the skin and protect the skincells from inside against sunlight-induced damage and reduce the levelof cutaneous matrix metalloproteases. Preferred respective ingredients,so called arylhydrocarbon receptor antagonists, are described in WO2007/128723, incorporated herein by reference. Preferred is2-benzylidene-5,6-dimethoxy-3,3-dimethylindan-1-one.

The UV filters cited below which can be used within the context of thepresent invention are preferred but naturally are not limiting.

UV filters which are preferably used are selected from the groupconsisting of

-   -   p-aminobenzoic acid    -   p-aminobenzoic acid ethyl ester (25 mol) ethoxylated (INCI name:        PEG-25 PABA)    -   p-dimethylaminobenzoic acid-2-ethylhexyl ester    -   p-aminobenzoic acid ethyl ester (2 mol) N-propoxylated    -   p-aminobenzoic acid glycerol ester    -   salicylic acid homomenthyl ester (homosalates) (Neo Heliopan®        HMS)    -   salicylic acid-2-ethylhexyl ester (Neo Heliopan® OS)    -   triethanolamine salicylate    -   4-isopropyl benzyl salicylate    -   anthranilic acid menthyl ester (Neo Heliopan® MA)    -   diisopropyl cinnamic acid ethyl ester    -   p-methoxycinnamic acid-2-ethylhexyl ester (Neo Heliopan® AV)    -   diisopropyl cinnamic acid methyl ester    -   p-methoxycinnamic acid isoamyl ester (Neo Heliopan® E 1000)    -   p-methoxycinnamic acid diethanolamine salt    -   p-methoxycinnamic acid isopropyl ester    -   2-phenylbenzimidazole sulfonic acid and salts (Neo Heliopan®        Hydro)    -   3-(4′-trimethylammonium) benzylidene bornan-2-one methyl sulfate    -   beta-imidazole-4(5)-acrylic acid (urocanic acid)    -   3-(4′-sulfo)benzylidene bornan-2-one and salts    -   3-(4′-methyl benzylidene)-D,L-camphor (Neo Heliopan® MBC)    -   3-benzylidene-D,L-camphor    -   N-[(2 and 4)-[2-(oxoborn-3-ylidene) methyl]benzyl] acrylamide        polymer    -   4,4′-[(6-[4-(1,1-dimethyl)aminocarbonyl)        phenylamino]-1,3,5-triazine-2,4-diyl)diimino]-bis-(benzoic        acid-2-ethylhexyl ester) (Uvasorb® HEB)    -   benzylidene malonate polysiloxane (Parsol® SLX)    -   glyceryl ethylhexanoate dimethoxycinnamate    -   dipropylene glycol salicylate    -   tris(2-ethylhexyl)-4,4′,4″-(1,3,5-triazine-2,4,6-triyltriimino)tribenzoate        (=2,4,6-trianilino-(p-carbo-2′-ethylhexyl-1′-oxy)-1,3,5-triazine)        (Uvinul® T150)

Broadband filters which are preferably combined with one or morecompounds of formula (I) in a preparation according to the presentinvention are selected from the group consisting of

-   -   2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan® 303)    -   ethyl-2-cyano-3,3′-diphenyl acrylate    -   2-hydroxy-4-methoxybenzophenone (Neo Heliopan® BB)    -   2-hydroxy-4-methoxybenzophenone-5-sulfonic acid    -   dihydroxy-4-methoxybenzophenone    -   2,4-dihydroxybenzophenone    -   tetrahydroxybenzophenone    -   2,2′-dihydroxy-4,4′-dimethoxybenzophenone    -   2-hydroxy-4-n-octoxybenzophenone    -   2-hydroxy-4-methoxy-4′-methyl benzophenone    -   sodium hydroxymethoxybenzophenone sulfonate    -   disodium-2,2′-dihydroxy-4,4′-dimethoxy-5,5′-disulfobenzophenone    -   phenol,        2-(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3(1,3,3,3-tetramethyl-1-(trimethylsilyl)oxy)disiloxyanyl)        propyl) (Mexoryl® XL)    -   2,2′-methylene        bis-(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)        phenol) (Tinosorb® M)    -   2,4-bis-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-1,3,5-triazine    -   2,4-bis-[{(4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine        (Tinosorb® S)    -   2,4-bis-[{(4-(3-sulfonato)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine        sodium salt    -   2,4-bis-[{(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine    -   2,4-bis-[{4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-[4-(2-methoxyethyl        carbonyl) phenylamino]-1,3,5-triazine    -   2,4-bis-[{4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy}phenyl]-6-[4-(2-ethylcarboxyl)        phenylamino]-1,3,5-triazine    -   2,4-bis-[{4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(1-methylpyrrol-2-yl)-1,3,5-triazine    -   2,4-bis-[{4-tris-(trimethylsiloxysilylpropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine    -   2,4-bis-[{4-(2″-methylpropenyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine    -   2,4-bis-[{4-(1′,1′,1′,3′,5′,5′,5′-heptamethylsiloxy-2″-methylpropyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine

UV-A filters filters which are preferably combined with one or morecompounds of formula (I) in a preparation according to the presentinvention are selected from the group consisting of

-   -   4-isopropyl dibenzoyl methane    -   terephthalylidene dibornane sulfonic acid and salts (Mexoryl®        SX)    -   4-t-butyl-4′-methoxydibenzoyl methane (avobenzone)/(Neo        Heliopan® 357)    -   phenylene bis-benzimidazyl tetrasulfonic acid disodium salt (Neo        Heliopan® AP)    -   2,2′-(1,4-phenylene)-bis-(1H-benzimidazole-4,6-disulfonic acid),        monosodium salt    -   2-(4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester        (Uvinul® A Plus)    -   indanylidene compounds in accordance with DE 100 55 940 A1 (=WO        2002 038537 A1)

UV filters which are more preferably combined with one or more compoundsof formula (I) in a preparation according to the present invention areselected from the group consisting of

-   -   p-aminobenzoic acid    -   3-(4′-trimethylammonium) benzylidene bornan-2-one methyl sulfate    -   salicylic acid homomenthyl ester (Neo Heliopan® HMS)    -   2-hydroxy-4-methoxybenzophenone (Neo Heliopan® BB)    -   2-phenylbenzimidazole sulfonic acid (Neo Heliopan® Hydro)    -   terephthalylidene dibornane sulfonic acid and salts (Mexoryl®        SX)    -   4-tert-butyl-4′-methoxydibenzoyl methane (Neo Heliopan® 357)    -   3-(4′-sulfo)benzylidene bornan-2-one and salts    -   2-ethylhexyl-2-cyano-3,3-diphenyl acrylate (Neo Heliopan® 303)    -   N-[(2 and 4)-[2-(oxoborn-3-ylidene) methyl]benzyl] acrylamide        polymer    -   p-methoxycinnamic acid-2-ethylhexyl ester (Neo Heliopan® AV)    -   p-aminobenzoic acid ethyl ester (25 mol) ethoxylated (INCI name:        PEG-25 PABA)    -   p-methoxycinnamic acid isoamyl ester (Neo Heliopan® E1000)    -   2,4,6-trianilino-(p-carbo-2′-ethylhexyl-1′-oxy)-1,3,5-triazine        (Uvinul® T150)    -   phenol,        2-(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3(1,3,3,3-tetramethyl-1-(trimethylsilyl)oxy)disiloxyanyl)        propyl) (Mexoryl® XL)    -   4,4′-[(6-[4-(1,1-dimethyl)aminocarbonyl)        phenylamino]-1,3,5-triazine-2,4-diyl)diimino]-bis-(benzoic        acid-2-ethylhexyl ester) (Uvasorb HEB)    -   3-(4′-methyl benzylidene)-D,L-camphor (Neo Heliopan® MBC)    -   3-benzylidene camphor    -   salicylic acid-2-ethylhexyl ester (Neo Heliopan® OS)    -   4-dimethylaminobenzoic acid-2-ethylhexyl ester (Padimate O)    -   hydroxy-4-methoxybenzophenone-5-sulfonic acid and Na salt    -   2,2′-methylene        bis-(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)        phenol) (Tinosorb® M)    -   phenylene bis-benzimidazyl tetrasulfonic acid disodium salt (Neo        Heliopan® AP)    -   2,4-bis-[{(4-(2-ethylhexyloxy)-2-hydroxy}phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine        (Tinosorb® S)    -   benzylidene malonate polysiloxane (Parsol® SLX)    -   menthyl anthranilate (Neo Heliopan® MA)    -   2-(4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl ester        (Uvinul® A Plus)    -   indanylidene compounds in accordance with DE 100 55 940 (=WO        02/38537).

Secondary Sun Protection Factors

Advantageous primary and also secondary sun protection factors arementioned in WO 2005 123101 A1. Advantageously, these preparationscontain at least one UVA filter and/or at least one UVB filter and/or atleast one inorganic pigment. The preparations may be present here invarious forms such as are conventionally used for sun protectionpreparations. Thus, they may be in form of a solution, an emulsion ofthe water-in-oil type (W/O) or of the oil-in-water type (O/W) or amultiple emulsion, for example of the water-in-oil-in-water type(W/O/W), a gel, a hydrodispersion, a solid stick or else an aerosol.

In a further preferred embodiment a formulation according to theinvention contains a total amount of sunscreen agents, i.e. inparticular UV filters and/or inorganic pigments (UV filtering pigments)so that the formulation according to the invention has a lightprotection factor of greater than or equal to 2 (preferably greater thanor equal to 5). Such formulations according to the invention areparticularly suitable for protecting the skin and hair.

Besides the groups of primary sun protection factors mentioned above,secondary sun protection factors of the antioxidant type may also beused. Secondary sun protection factors of the antioxidant type interruptthe photochemical reaction chain which is initiated when UV rayspenetrate into the skin. Typical examples are amino acids (for exampleglycine, histidine, tyrosine, tryptophane) and derivatives thereof,imidazoles (for example urocanic acid) and derivatives thereof,peptides, such as D,L-carnosine, D-carnosine, L-carnosine andderivatives thereof (for example anserine), carotinoids, carotenes (forexample alpha-carotene, beta-carotene, lycopene) and derivativesthereof, chlorogenic acid and derivatives thereof, liponic acid andderivatives thereof (for example dihydroliponic acid), aurothioglucose,propylthiouracil and other thiols (for example thioredoxine,glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl,methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl,alpha-linoleyl, cholesteryl and glyceryl esters thereof) and theirsalts, dilaurylthiodipropionate, distearylthiodipropionate,thiodipropionic acid and derivatives thereof (esters, ethers, peptides,lipids, nucleotides, nucleosides and salts) and sulfoximine compounds(for example butionine sulfoximines, homocysteine sulfoximine, butioninesulfones, penta-, hexa- and hepta-thionine sulfoximine) in very smallcompatible dosages, also (metal) chelators (for examplealpha-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrine),alpha-hydroxy acids (for example citric acid, lactic acid, malic acid),humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTAand derivatives thereof, unsaturated fatty acids and derivatives thereof(for example linoleic acid, oleic acid), folic acid and derivativesthereof, ubiquinone and ubiquinol and derivatives thereof, vitamin C andderivatives thereof (for example ascorbyl palmitate, Mg ascorbylphosphate, ascorbyl acetate), tocopherols and derivatives (for examplevitamin E acetate), vitamin A and derivatives (vitamin A palmitate) andconiferyl benzoate of benzoin resin, rutinic acid and derivativesthereof, glycosyl rutin, ferulic acid, furfurylidene glucitol,carnosine, butyl hydroxytoluene, butyl hydroxyanisole, nordihydroguaiacresin acid, nordihydroguaiaretic acid, trihydroxybutyrophenone, uricacid and derivatives thereof, mannose and derivatives thereof,superoxide dismutase, titanium dioxide (for example dispersions inethanol), zinc and derivatives thereof (for example ZnO, ZnSO₄),selenium and derivatives thereof (for example selenium methionine),stilbenes and derivatives thereof (for example stilbene oxide,trans-stilbene oxide) and derivatives of these active substancessuitable for the purposes of the invention (salts, esters, ethers,sugars, nucleotides, nucleosides, peptides and lipids).

Advantageous inorganic secondary light protection pigments are finelydispersed metal oxides and metal salts which are also mentioned in WO2005 123101 A1. The total quantity of inorganic pigments, in particularhydrophobic inorganic micro-pigments in the finished cosmeticpreparation according to the present invention is advantageously from0.1 to 30% by weight, preferably 0.5 to 10.0% by weight, in each casebased on the total weight of the preparation.

Also preferred are particulate UV filters or inorganic pigments, whichcan optionally be hydrophobed, can be used, such as the oxides oftitanium (TiO₂), zinc (ZnO), iron (Fe₂O₃), zirconium (ZrO₂), silicon(SiO₂), manganese (e.g. MnO), aluminium (Al₂O₃), cerium (e.g. Ce₂O₃)and/or mixtures thereof.

Anti-Ageing Actives

In the context of the invention, anti-ageing or biogenic agents are, forexample antioxidants, matrix-metalloproteinase inhibitrors (MMPI), skinmoisturizing agents, glycosaminglycan stimulkators, anti-inflammatoryagents, TRPV1 antagonists and plant extracts.

Antioxidants. amino acids (preferably glycine, histidine, tyrosine,tryptophane) and derivatives thereof, imidazoles (preferably urocanicacid) and derivatives thereof, peptides, preferably D,L-carnosine,D-carnosine, L-carnosine and derivatives thereof (preferably anserine),carnitine, creatine, matrikine peptides (preferablylysyl-threonyl-threonyl-lysyl-serine) and palmitoylated pentapeptides,carotenoids, carotenes (preferably alpha-carotene, beta-carotene,lycopene) and derivatives thereof, lipoic acid and derivatives thereof(preferably dihydrolipoic acid), aurothioglucose, propyl thiouracil andother thiols (preferably thioredoxine, glutathione, cysteine, cystine,cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl andlauryl, palmitoyl, oleyl, gamma-linoleyl, cholesteryl, glyceryl andoligoglyceryl esters thereof) and salts thereof, dilaurylthiodipropionate, distearyl thiodipropionate, thiodipropionic acid andderivatives thereof (preferably esters, ethers, peptides, lipids,nucleotides, nucleosides and salts) and sulfoximine compounds(preferably buthionine sulfoximines, homocysteine sulfoximine,buthionine sulfones, penta-, hexa-, heptathionine sulfoximine) in verysmall tolerated doses (e.g. pmol to μmol/kg), also (metal) chelators(preferably alpha-hydroxy fatty acids, palmitic acid, phytic acid,lactoferrin, alpha-hydroxy acids (preferably citric acid, lactic acid,malic acid), humic acid, bile acid, bile extracts, tannins, bilirubin,biliverdin, EDTA, EGTA and derivatives thereof), unsaturated fatty acidsand derivatives thereof (preferably gamma-linolenic acid, linoleic acid,oleic acid), folic acid and derivatives thereof, ubiquinone andderivatives thereof, ubiquinol and derivatives thereof, vitamin C andderivatives (preferably ascorbyl palmitate, Mg ascorbyl phosphate,ascorbyl acetate, ascorbyl glucoside), tocopherols and derivatives(preferably vitamin E acetate), vitamin A and derivatives (vitamin Apalmitate) and coniferyl benzoate of benzoic resin, rutinic acid andderivatives thereof, flavonoids and glycosylated precursors thereof, inparticular quercetin and derivatives thereof, preferably alpha-glucosylrutin, rosmarinic acid, carnosol, carnosolic acid, resveratrol, caffeicacid and derivatives thereof, sinapic acid and derivatives thereof,ferulic acid and derivatives thereof, curcuminoids, chlorogenic acid andderivatives thereof, retinoids, preferably retinyl palmitate, retinol ortretinoin, ursolic acid, levulinic acid, butyl hydroxytoluene, butylhydroxyanisole, nordihydroguaiac acid, nordihydroguaiaretic acid,trihydroxybutyrophenone, uric acid and derivatives thereof, mannose andderivatives thereof, zinc and derivatives thereof (preferably ZnO,ZnSO₄), selenium and derivatives thereof (preferably seleniummethionine), superoxide dismutase, stilbenes and derivatives thereof(preferably stilbene oxide, trans-stilbene oxide) and the derivatives(salts, esters, ethers, sugars, nucleotides, nucleosides, peptides andlipids) of these cited active ingredients which are suitable accordingto the invention or extracts or fractions of plants having anantioxidant effect, preferably green tea, rooibos, honeybush, grape,rosemary, sage, melissa, thyme, lavender, olive, oats, cocoa, ginkgo,ginseng, liquorice, honeysuckle, sophora, pueraria, pinus, citrus,Phyllanthus emblica or St. John's wort, grape seeds, wheat germ,Phyllanthus emblica, coenzymes, preferably coenzyme Q10, plastoquinoneand menaquinone. Preferred antioxidants are selected from the groupconsisting of vitamin A and derivatives, vitamin C and derivatives,tocopherol and derivatives, preferably tocopheryl acetate, andubiquinone.

Matrix-Metalloproteinase inhibitors (MMPI). Preferred compositionscomprise matrix-metalloproteinase inhibitors, especially thoseinhibiting matrix-metalloproteinases enzymatically cleaving collagen,selected from the group consisting of: ursolic acid, retinyl palmitate,propyl gallate, precocenes,6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran,3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran,benzamidine hydrochloride, the cysteine proteinase inhibitorsN-ethylmalemide and epsilon-amino-n-caproic acid of the serinproteaseinhibitors: phenylmethylsufonylfluoride, collhibin (company Pentapharm;INCI: hydrolysed rice protein), oenotherol (company Soliance; INCI:propylene glycol, aqua, Oenothera biennis root extract, ellagic acid andellagitannins, for example from pomegranate), phosphoramidonehinokitiol, EDTA, galardin, EquiStat (company Collaborative Group; applefruit extract, soya seed extract, ursolic acid, soya isoflavones andsoya proteins), sage extracts, MDI (company Atrium; INCI:glycosaminoglycans), fermiskin (company Silab/Mawi; INCI: water andlentinus edodes extract), actimp 1.9.3 (company Expanscience/Rahn; INCI:hydrolysed lupine protein), lipobelle soyaglycone (company Mibelle;INCI: alcohol, polysorbate 80, lecithin and soy isoflavones), extractsfrom green and black tea and further plant extracts, which are listed inWO 02 069992 A1 (see tables 1-12 there, incorporated herein byreference), proteins or glycoproteins from soya, hydrolysed proteinsfrom rice, pea or lupine, plant extracts which inhibit MMPs, preferablyextracts from shitake mushrooms, extracts from the leaves of theRosaceae family, sub-family Rosoideae, quite particularly extracts ofblackberry leaf (preferably as described in WO 2005 123101 A1,incorporated herein by reference) as e.g. SymMatrix (company Symrise,INCI: Maltodextrin, Rubus Fruticosus (Blackberry) Leaf Extract).Preferred actives of are selected from the group consisting of retinylpalmitate, ursolic acid, extracts from the leaves of the Rosaceaefamily, sub-family Rosoideae, genistein and daidzein.

Skin-moisturizing agents. Preferred skin moisturizing agents areselected from the group consisting of alkane diols or alkane triolscomprising 3 to 12 carbon atoms, preferably C₃-C₁₀-alkane diols andC₃-C₁₀-alkane triols. More preferably the skin moisturizing agents areselected from the group consisting of: glycerol, 1,2-propylene glycol,1,2-butylene glycol, 1,3-butylene glycol, 1,2-pentanediol,1,2-hexanediol, 1,2-octanediol and 1,2-decanediol.

Glycosaminoglycan stimulators. Preferred compositions comprisesubstances stimulating the synthesis of glycosaminoglycans selected fromthe group consisting of hyaluronic acid and derivatives or salts,Subliskin (Sederma, INCI: Sinorhizobium Meliloti Ferment Filtrate, CetylHydroxyethylcellulose, Lecithin), Hyalufix (BASF, INCI: Water, ButyleneGlycol, Alpinia galanga leaf extract, Xanthan Gum, Caprylic/CapricTriglyceride), Stimulhyal (Soliance, INCI: Calcium ketogluconate),Syn-Glycan (DSM, INCI: Tetradecyl Aminobutyroylvalylaminobutyric UreaTrifluoroacetate, Glycerin, Magnesium chloride), Kalpariane (BiotechMarine), DC Upregulex (Distinctive Cosmetic Ingredients, INCI: Water,Butylene Glycol, Phospholipids, Hydrolyzed Sericin), glucosamine,N-acetyl glucosamine, retinoids, preferably retinol and vitamin A,Arctium lappa fruit extract, Eriobotrya japonica extract, Genkwanin,N-Methyl-L-serine, (−)-alpha-bisabolol or synthetic alpha-bisabolol suchas e.g. Dragosantol and Dragosantol 100 from Symrise, oat glucan,Echinacea purpurea extract and soy protein hydrolysate. Preferredactives are selected from the group consisting of hyaluronic acid andderivatives or salts, retinol and derivatives, (−)-alpha-bisabolol orsynthetic alpha-bisabolol such as e.g. Dragosantol and Dragosantol 100from Symrise, oat glucan, Echinacea purpurea extract, SinorhizobiumMeliloti Ferment Filtrate, Calcium ketogluconate, Alpinia galanga leafextract and tetradecyl aminobutyroylvalylaminobutyric ureatrifluoroacetate.

Anti-inflammatory agents. The compositions may also containanti-inflammatory and/or redness and/or itch ameliorating ingredients,in particular steroidal substances of the corticosteroid type selectedfrom the group consisting of hydrocortisone, dexamethasone,dexamethasone phosphate, methyl prednisolone or cortisone, areadvantageously used as anti-inflammatory active ingredients or activeingredients to relieve reddening and itching, the list of which can beextended by the addition of other steroidal anti-inflammatories.Non-steroidal anti-inflammatories can also be used. Examples which canbe cited here are oxicams such as piroxicam or tenoxicam; salicylatessuch as aspirin, disalcid, solprin or fendosal; acetic acid derivativessuch as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin orclindanac; fenamates such as mefenamic, meclofenamic, flufenamic orniflumic; propionic acid derivatives such as ibuprofen, naproxen,benoxaprofen or pyrazoles such as phenylbutazone, oxyphenylbutazone,febrazone or azapropazone. Anthranilic acid derivatives, in particularavenanthramides described in WO 2004 047833 A1, are preferred anti-itchingredients in a composition according to the present invention.

Also useful are natural or naturally occurring anti-inflammatorymixtures of substances or mixtures of substances that alleviatereddening and/or itching, in particular extracts or fractions fromcamomile, Aloe vera, Commiphora species, Rubia species, willow,willow-herb, oats, calendula, arnica, St John's wort, honeysuckle,rosemary, Passiflora incarnata, witch hazel, ginger or Echinacea;preferably selected from the group consisting of extracts or fractionsfrom camomile, Aloe vera, oats, calendula, arnica, honeysuckle,rosemary, witch hazel, ginger or Echinacea, and/or pure substances,preferably alpha-bisabolol, apigenin, apigenin-7-glucoside, gingerols,shogaols, gingerdiols, dehydrogingerdiones, paradols, natural ornaturally occuring avenanthramides, preferably tranilast, avenanthramideA, avenanthramide B, avenanthramide C, non-natural or non-naturallyoccuring avenanthramides, preferably dihydroavenanthramide D,dihydroavenanthramide E, avenanthramide D, avenanthramide E,avenanthramide F, boswellic acid, phytosterols, glycyrrhizin, glabridinand licochalcone A; preferably selected from the group consisting ofalpha-bisabolol, natural avenanthramides, non-natural avenanthramides,preferably dihydroavenanthramide D (as described in WO 2004 047833 A1),boswellic acid, phytosterols, glycyrrhizin, and licochalcone A, and/orallantoin, panthenol, lanolin, (pseudo-)ceramides [preferably Ceramide2, hydroxypropyl bispalmitamide MEA, cetyloxypropyl glycerylmethoxypropyl myristamide, N-(1-hexadecanoyl)-4-hydroxy-L-proline(1-hexadecyl) ester, hydroxyethyl palmityl oxyhydroxypropylpalmitamide], glycosphingolipids, phytosterols, chitosan, mannose,lactose and β-glucans, in particular 1,3-1,4-β-glucan from oats.

TRPV1 antagonists. Suitable compounds which reduce the hypersensitivityof skin nerves based on their action as TRPV1 antagonists, encompasse.g. trans-4-tert-butyl cyclohexanol as described in WO 2009 087242 A1,or indirect modulators of TRPV1 by an activation of the μ-receptor, e.g.acetyl tetrapeptide-15, are preferred.

Botanical extracts. The compositions may also contain various extractsof plants, such as for example extracts of Ginkgo biloba, Oleaceaeuropensis, Glyzyrrhiza glabra, Vacciniurn myrtillus, Trifoliumpratense, Litchi sinensis, Vitis, vinifera, Brassica oleracea, Punicagranatum, Petroselinium crispum, Centella asiatica, Passifloraincarnata, Medicago sativa, Melissa officinalis, Valeriana officinalis,Castanea sativa, Salix alba and Hapagophytum procumbens.

Cooling Agents

The compositions may also contain one or more substances with aphysiological cooling effect (cooling agents), which are preferablyselected here from the following list: menthol and menthol derivatives(for example L-menthol, D-menthol, racemic menthol, isomenthol,neoisomenthol, neomenthol) menthylethers (for example(I-menthoxy)-1,2-propandiol, (I-menthoxy)-2-methyl-1,2-propandiol,I-menthyl-methylether), menthylesters (for example menthylformiate,menthylacetate, menthylisobutyrate, menthyllactates,L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(2-methoxy)acetate,menthyl-(2-methoxyethoxy)acetate, menthylpyroglutamate),menthylcarbonates (for example menthylpropyleneglycolcarbonate,menthylethyleneglycolcarbonate, menthylglycerolcarbonate or mixturesthereof), the semi-esters of menthols with a dicarboxylic acid orderivatives thereof (for example mono-menthylsuccinate,mono-menthylglutarate, mono-menthylmalonate, O-menthyl succinic acidester-N,N-(dimethyl)amide, O-menthyl succinic acid ester amide),menthanecarboxylic acid amides (in this case preferablymenthanecarboxylic acid-N-ethylamide [WS3] orN^(α)-(menthanecarbonyl)glycinethylester [WS5], as described in U.S.Pat. No. 4,150,052, menthanecarboxylic acid-N-(4-cyanophenyl)amide ormenthanecarboxylic acid-N-(4-cyanomethylphenyl)amide as described in WO2005 049553 A1, methanecarboxylic acid-N-(alkoxyalkyl)amides), menthoneand menthone derivatives (for example L-menthone glycerol ketal),2,3-dimethyl-2-(2-propyl)-butyric acid derivatives (for example2,3-dimethyl-2-(2-propyl)-butyric acid-N-methylamide [WS23]), isopulegolor its esters (I-(−)-isopulegol, I-(−)-isopulegolacetate), menthanederivatives (for example p-menthane-3,8-diol), cubebol or synthetic ornatural mixtures, containing cubebol, pyrrolidone derivatives ofcycloalkyldione derivatives (for example3-methyl-2(1-pyrrolidinyl)-2-cyclopentene-1-one) ortetrahydropyrimidine-2-one (for example iciline or related compounds, asdescribed in WO 2004/026840), further carboxamides (for exampleN-(2-(pyridin-2-yl)ethyl)-3-p-menthanecarboxamide or related compounds),(1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-isopropyl)cyclohexane-carboxamide[WS12], oxamates (preferably those described in EP 2033688 A2).

Anti-Microbial Agents

Suitable anti-microbial agents are, in principle, all substanceseffective against Gram-positive bacteria, such as, for example, 4-hydroxybenzoic acid and its salts and esters,N-(4-chlorophenyl)-N′-(3,4- dichlorophenyl)urea,2,4,4′-trichloro-2′-hydroxy-diphenyl ether (triclosan),4-chloro-3,5-dimethyl-phenol, 2,2′-methylenebis(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)phenol,2-benzyl-4-chloro-phenol, 3-(4-chlorophenoxy)-1,2-propanediol,3-iodo-2-propynyl butylcarbamate, chlorhexidine,3,4,4′-trichlorocarbanilide (TTC), antibacterial fragrances, thymol,thyme oil, eugenol, oil of cloves, menthol, mint oil, farnesol,phenoxyethanol, glycerol monocaprate, glycerol monocaprylate, glycerolmonolaurate (GML), diglycerol monocaprate (DMC), salicylic acidN-alkylamides, such as, for example, n-octylsalicylamide orn-decylsalicylamide.

Enzyme Inhibitors

Suitable enzyme inhibitors are, for example, esterase inhibitors. Theseare preferably trialkyl citrates, such as trimethyl citrate, tripropylcitrate, triisopropyl citrate, tributyl citrate and, in particular,triethyl citrate (Hydagen CAT). The substances inhibit enzyme activity,thereby reducing the formation of odour. Other substances which aresuitable esterase inhibitors are sterol sulfates or phosphates, such as,for example, lanosterol, cholesterol, campesterol, stigmasterol andsitosterol sulfate or phosphate, dicarboxylic acids and esters thereof,such as, for example, glutaric acid, monoethyl glutarate, diethylglutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acidand diethyl malonate, hydroxycarboxylic acids and esters thereof, suchas, for example, citric acid, malic acid, tartaric acid or diethyltartrate, and zinc glycinate.

Odour Absorbers and Antiperspirant Active Agents

Suitable odour absorbers are substances which are able to absorb andlargely retain odour-forming compounds. They lower the partial pressureof the individual components, thus also reducing their rate ofdiffusion. It is important that perfumes must remain unimpaired in thisprocess. Odour absorbers are not effective against bacteria. Theycomprise, for example, as main constituent, a complex zinc salt ofricinoleic acid or specific, largely odour-neutral fragrances which areknown to the person skilled in the art as “fixatives”, such as, forexample, extracts of labdanum or styrax or certain abietic acidderivatives. The odour masking agents are fragrances or perfume oils,which, in addition to their function as odour masking agents, give thedeodorants their respective fragrance note. Perfume oils which may bementioned are, for example, mixtures of natural and syntheticfragrances. Natural fragrances are extracts from flowers, stems andleaves, fruits, fruit peels, roots, woods, herbs and grasses, needlesand branches, and resins and balsams. Also suitable are animal products,such as, for example, civet and castoreum. Typical synthetic fragrancecompounds are products of the ester, ether, aldehyde, ketone, alcohol,and hydrocarbon type. Fragrance compounds of the ester type are, forexample, benzyl acetate, p-tert-butylcyclohexyl acetate, linalylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, allylcyclohexylpropionate, styrallyl propionate and benzyl salicylate. Theethers include, for example, benzyl ethyl ether, and the aldehydesinclude, for example, the linear alkanals having 8 to 18 carbon atoms,citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde,hydroxycitronellal, lilial and bourgeonal, the ketones include, forexample, the ionones and methyl cedryl ketone, the alcohols includeanethole, citronellol, eugenol, isoeugenol, geraniol, linaool,phenylethyl alcohol and terpineol, and the hydrocarbons include mainlythe terpenes and balsams. Preference is, however, given to usingmixtures of different fragrances which together produce a pleasingfragrance note. Essential oils of relatively low volatility, which aremostly used as aroma components, are also suitable as perfume oils, e.g.sage oil, camomile oil, oil of cloves, melissa oil, mint oil, cinnamonleaf oil, linden flower oil, juniperberry oil, vetiver oil, olibanumoil, galbanum oil, labdanum oil and lavandin oil. Preference is given tousing bergamot oil, dihydromyrcenol, lilial, lyral, citronellol,phenylethyl alcohol, α-hexylcinnamaldehyde, geraniol, benzylacetone,cyclamen aldehyde, linalool, boisambrene forte, ambroxan, indole,hedione, sandelice, lemon oil, mandarin oil, orange oil, allyl amylglycolate, cyclovertal, lavandin oil, clary sage oil, β-damascone,geranium oil bourbon, cyclohexyl salicylate, Vertofix coeur,iso-E-super, Fixolide NP, evernyl, iraldein gamma, phenylacetic acid,geranyl acetate, benzyl acetate, rose oxide, romilat, irotyl andfloramat alone or in mixtures.

Suitable astringent antiperspirant active ingredients are primarilysalts of aluminium, zirconium or of zinc. Such suitable antihydroticactive ingredients are, for example, aluminium chloride, aluminiumchlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohydrateand complex compounds thereof, e.g. with 1,2- propylene glycol,aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminiumzirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate,aluminium zirconium pentachlorohydrate and complex compounds thereof,e.g. with amino acids, such as glycine.

Film Formers and Anti-Dandruff Agents

Standard film formers are, for example, chitosan, microcrystallinechitosan, quaternized chitosan, polyvinyl pyrrolidone, vinylpyrrolidone/vinyl acetate copolymers, polymers of the acrylic acidseries, quaternary cellulose derivatives, collagen, hyaluronic acid andsalts thereof and similar compounds.

Suitable antidandruff agents are Pirocton Olamin(1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)-pyridinonemonoethanolamine salt), Baypival® (Climbazole), Ketoconazol®(4-acetyl-1-{4-[2-(2,4-dichlorophenyl) r-2-(1H-imidazol-1-ylmethyl)-1,3-dioxylan-c-4-ylmethoxyphenyl}-piperazine, ketoconazole,elubiol, selenium disulfide, colloidal sulfur, sulfur polyethyleneglycol sorbitan monooleate, sulfur ricinol polyethoxylate, sulfur tardistillate, salicylic acid (or in combination with hexachlorophene),undecylenic acid, monoethanolamide sulfosuccinate Na salt, Lamepon® UD(protein/undecylenic acid condensate), zinc pyrithione, aluminiumpyrithione and magnesium pyrithione/dipyrithione magnesium sulfate.

Carriers and Hydrotropes

Preferred cosmetics carrier materials are solid or liquid at 25° C. and1013 mbar (including highly viscous substances) as for example glycerol,1,2-propylene glycol, 1,2-butylene glycol, 1,3-propylene glycol,1,3-butylene glycol, ethanol, water and mixtures of two or more of saidliquid carrier materials with water. Optionally, these preparationsaccording to the invention may be produced using preservatives orsolubilizers. Other preferred liquid carrier substances, which may be acomponent of a preparation according to the invention are selected fromthe group consisting of oils such as vegetable oil, neutral oil andmineral oil.

Preferred solid carrier materials, which may be a component of apreparation according to the invention are hydrocolloids, such asstarches, degraded starches, chemically or physically modified starches,dextrins, (powdery) maltodextrins (preferably with a dextrose equivalentvalue of 5 to 25, preferably of 10-20), lactose, silicon dioxide,glucose, modified celluloses, gum arabic, ghatti gum, traganth, karaya,carrageenan, pullulan, curdlan, xanthan gum, gellan gum, guar flour,carob bean flour, alginates, agar, pectin and inulin and mixtures of twoor more of these solids, in particular maltodextrins (preferably with adextrose equivalent value of 15-20), lactose, silicon dioxide and/orglucose.

In addition, hydrotropes, for example ethanol, isopropyl alcohol orpolyols, may be used to improve flow behaviour. Suitable polyolspreferably contain 2 to 15 carbon atoms and at least two hydroxylgroups. The polyols may contain other functional groups, more especiallyamino groups, or may be modified with nitrogen. Typical examples are

-   -   glycerol;    -   alkylene glycols such as, for example, ethylene glycol,        diethylene glycol, propylene glycol, butylene glycol, hexylene        glycol and polyethylene glycols with an average molecular weight        of 100 to 1000 Dalton;    -   technical oligoglycerol mixtures with a degree of        self-condensation of 1.5 to 10, such as for example technical        diglycerol mixtures with a diglycerol content of 40 to 50% by        weight;    -   methylol compounds such as, in particular, trimethylol ethane,        trimethylol propane, trimethylol butane, pentaerythritol and        dipentaerythritol;    -   lower alkyl glucosides, particularly those containing 1 to 8        carbon atoms in the alkyl group, for example methyl and butyl        glucoside;    -   sugar alcohols containing 5 to 12 carbon atoms, for example        sorbitol or mannitol,    -   sugars containing 5 to 12 carbon atoms, for example glucose or        sucrose;    -   amino sugars, for example glucamine;    -   dialcoholamines, such as diethanolamine or        2-aminopropane-1,3-diol.

Preservatives

Suitable preservatives are, for example, phenoxyethanol, formaldehydesolution, parabens, pentanediol or sorbic acid and the other classes ofcompounds listed in Appendix 6, Parts A and B of the Kosmetikverordnung(“Cosmetics Directive”).

Perfume Oils and Fragrances

Suitable perfume oils are mixtures of natural and synthetic perfumes.Natural perfumes include the extracts of blossoms (lily, lavender, rose,jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli,petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel(bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom,costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood,cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage,thyme), needles and branches (spruce, fir, pine, dwarf pine), resins andbalsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animalraw materials, for example civet and beaver, may also be used. Typicalsynthetic perfume compounds are products of the ester, ether, aldehyde,ketone, alcohol and hydrocarbon type. Examples of perfume compounds ofthe ester type are benzyl acetate, phenoxyethyl isobutyrate,p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzylcarbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzylformate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate,styrallyl propionate and benzyl salicylate. Ethers include, for example,benzyl ethyl ether while aldehydes include, for example, the linearalkanals containing 8 to 18 carbon atoms, citral, citronellal,citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxy-citronellal,lilial and bourgeonal. Examples of suitable ketones are the ionones,

-isomethylionone and methyl cedryl ketone. Suitable alcohols areanethol, citronellol, eugenol, isoeugenol, geraniol, linalool,phenylethyl alcohol and terpineol. The hydrocarbons mainly include theterpenes and balsams. However, it is preferred to use mixtures ofdifferent perfume compounds which, together, produce an agreeableperfume. Other suitable perfume oils are essential oils of relativelylow volatility which are mostly used as aroma components. Examples aresage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leafoil, lime-blossom oil, juniper berry oil, vetiver oil, olibanum oil,galbanum oil, ladanum oil and lavendin oil. The following are preferablyused either individually or in the form of mixtures: bergamot oil,dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol,hexylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde,linalool, Boisambrene Forte, Ambroxan, indole, hedione, sandelice,citrus oil, mandarin oil, orange oil, allylamyl glycolate, cyclovertal,lavendin oil, clary oil, damascone, geranium oil bourbon, cyclohexylsalicylate, Vertofix Coeur, Iso-E-Super, Fixolide NP, evernyl, iraldeingamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide,romillat, irotyl and floramat.

Dyes

Suitable dyes are any of the substances suitable and approved forcosmetic purposes as listed, for example, in the publication“Kosmetische Färbemittel” of the Farbstoff-kommission der DeutschenForschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, pages 81 to 106.Examples include cochineal red A (C.I. 16255), patent blue V (C.I.42051), indigotin (C.I. 73015), chlorophyllin (C.I. 75810), quinolineyellow (C.I. 47005), titanium dioxide (C.I. 77891), indanthrene blue RS(C.I. 69800) and madder lake (C.I. 58000). Luminol may also be presentas a luminescent dye. Advantageous coloured pigments are for exampletitanium dioxide, mica, iron oxides (e.g. Fe₂O₃ Fe₃O₄, FeO(OH)) and/ortin oxide. Advantageous dyes are for example carmine, Berlin blue,chromium oxide green, ultramarine blue and/or manganese violet.

Preferred compositions according to the present inventions are selectedfrom the group of products for treatment, protecting, care and cleansingof the skin and/or hair or as a make-up product, preferably as aleave-on product (meaning that the one or more compounds of formula (I)stay on the skin and/or hair for a longer period of time, compared torinse-off products, so that the moisturizing and/or anti-ageing and/orwound healing promoting action thereof is more pronounced).

The formulations according to the invention are preferably in the formof an emulsion, e.g. W/O (water-in-oil), O/W (oil-in-water), W/O/W(water-in-oil-in-water), O/W/O (oil-in-water-in-oil) emulsion, PITemulsion, Pickering emulsion, emulsion with a low oil content, micro- ornanoemulsion, a solution, e.g. in oil (fatty oils or fatty acid esters,in particular C₆-C₃₂ fatty acid C₂-C₃₀ esters) or silicone oil,dispersion, suspension, creme, lotion or milk, depending on theproduction method and ingredients, a gel (including hydrogel,hydrodispersion gel, oleogel), spray (e.g. pump spray or spray withpropellant) or a foam or an impregnating solution for cosmetic wipes, adetergent, e.g. soap, synthetic detergent, liquid washing, shower andbath preparation, bath product (capsule, oil, tablet, salt, bath salt,soap, etc.), effervescent preparation, a skin care product such as e.g.an emulsion (as described above), ointment, paste, gel (as describedabove), oil, balsam, serum, powder (e.g. face powder, body powder), amask, a pencil, stick, roll-on, pump, aerosol (foaming, non-foaming orpost-foaming), a deodorant and/or antiperspirant, mouthwash and mouthrinse, a foot care product (including keratolytic, deodorant), an insectrepellent, a sunscreen, aftersun preparation, a shaving product,aftershave balm, pre- and aftershave lotion, a depilatory agent, a haircare product such as e.g. shampoo (including 2-in-1 shampoo,anti-dandruff shampoo, baby shampoo, shampoo for dry scalps,concentrated shampoo), conditioner, hair tonic, hair water, hair rinse,styling creme, pomade, perm and setting lotion, hair spray, styling aid(e.g. gel or wax), hair smoothing agent (detangling agent, relaxer),hair dye such as e.g. temporary direct-dyeing hair dye, semi-permanenthair dye, permanent hair dye, hair conditioner, hair mousse, eye careproduct, make-up, make-up remover or baby product.

The formulations according to the invention are particularly preferablyin the form of an emulsion, in particular in the form of a W/O, O/W,W/O/W, O/W/O emulsion, PIT emulsion, Pickering emulsion, emulsion with alow oil content, micro- or nanoemulsion, a gel (including hydrogel,hydrodispersion gel, oleogel), a solution e.g. in oil (fatty oils orfatty acid esters, in particular C₆-C₃₂ fatty acid C₂-C₃₀ esters)) orsilicone oil, or a spray (e.g. pump spray or spray with propellant).

Auxiliary substances and additives can be included in quantities of 5 to99% b.w., preferably 10 to 80% b.w., based on the total weight of theformulation. The amounts of cosmetic or dermatological auxiliary agentsand additives and perfume to be used in each case can easily bedetermined by the person skilled in the art by simple trial and error,depending on the nature of the particular product.

The preparations can also contain water in a quantity of up to 99% b.w.,preferably 5 to 80% b.w., based on the total weight of the preparation.

Food Compositions

Another object of the present invention is to provide food compositions,which comprise the composition with stabilized taste and/or odoraccording to the present invention.

Food compositions according to the invention are any preparations orcompositions which are suitable for consumption and are used fornutrition or enjoyment purposes, and are generally products which areintended to be introduced into the human or animal oral cavity, toremain there for a certain time and then either be eaten (e.g.ready-to-eat foodstuffs or feeds, see also herein below) or removed fromthe oral cavity again (e.g. chewing gums). Such products include anysubstances or products which in the processed, partially processed orunprocessed state are to be ingested by humans or animals. They alsoinclude substances which are added to orally consumable products duringtheir manufacture, preparation or treatment and which are intended to beintroduced into the human or animal oral cavity.

The food compositions according to the invention also include substanceswhich in the unchanged, treated or prepared state are to be swallowed bya human or animal and then digested; in this respect, the orallyconsumable products according to the invention also include casings,coatings or other encapsulations which are to be swallowed at the sametime or which may be expected to be swallowed. The expression “orallyconsumable product” covers ready-to-eat foodstuffs and feeds, that is tosay foodstuffs or feeds that are already complete in terms of thesubstances that are important for the taste. The expressions“ready-to-eat foodstuff” and “ready-to-eat feed” also include drinks aswell as solid or semi-solid ready-to-eat foodstuffs or feeds. Exampleswhich may be mentioned are frozen products, which must be thawed andheated to eating temperature before they are eaten. Products such asyoghurt or ice-cream as well as chewing gums or hard caramels are alsoincluded among the ready-to-eat foodstuffs or feeds.

Preferred food compositions according to the invention also include“semi-finished products”. Within the context of the present text, asemi-finished product is to be understood as being an orally consumableproduct which, because of a very high content of flavourings andtaste-imparting substances, is unsuitable for use as a ready-to-eatorally consumable product (in particular foodstuff or feed). Only bymixing with at least one further constituent (e.g. by reducing theconcentration of the flavourings and taste-imparting substances inquestion) and optionally further process steps (e.g. heating, freezing)is the semi-finished product converted into a ready-to-eat orallyconsumable product (in particular foodstuff or feed). Examples ofsemi-finished products which may be mentioned here are

Food composition according to the invention preferably comprises one ormore preparations for nutrition or enjoyment purposes. These include inparticular (reduced-calorie) baked goods (e.g. bread, dry biscuits,cakes, other baked articles), confectionery (e.g. chocolates, chocolatebars, other products in bar form, fruit gums, dragées, hard and softcaramels, chewing gum), non-alcoholic drinks (e.g. cocoa, coffee, greentea, black tea, (green, black) tea drinks enriched with (green, black)tea extracts, rooibos tea, other herbal teas, fruit-containing softdrinks, isotonic drinks, refreshing drinks, nectars, fruit and vegetablejuices, fruit or vegetable juice preparations), instant drinks (e.g.instant cocoa drinks, instant tea drinks, instant coffee drinks), meatproducts (e.g. ham, fresh sausage or raw sausage preparations, spiced ormarinated fresh or salt meat products), eggs or egg products (dried egg,egg white, egg yolk), cereal products (e.g. breakfast cereals, mueslibars, precooked ready-to-eat rice products), dairy products (e.g.full-fat or reduced-fat or fat-free milk drinks, rice pudding, yoghurt,kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey,butter, buttermilk, partially or completely hydrolysedmilk-protein-containing products), products made from soy protein orother soybean fractions (e.g. soy milk and products produced therefrom,drinks containing isolated or enzymatically treated soy protein, drinkscontaining soy flour, preparations containing soy lecithin, fermentedproducts such as tofu or tempeh or products produced therefrom andmixtures with fruit preparations and optionally flavours), fruitpreparations (e.g. jams, sorbets, fruit sauces, fruit fillings),vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozenvegetables, precooked vegetables, boiled-down vegetables), snacks (e.g.baked or fried potato crisps or potato dough products, maize- orgroundnut-based extrudates), fat- and oil-based products or emulsionsthereof (e.g. mayonnaise, remoulade, dressings, in each case full-fat orreduced-fat), other ready-made dishes and soups (e.g. dried soups,instant soups, precooked soups), spices, spice mixtures and inparticular seasonings which are used, for example, in the snacks field,sweetener preparations, tablets or sachets, other preparations forsweetening or whitening drinks or other foods. The preparations withinthe scope of the invention can also be used in the form of semi-finishedproducts for the production of further preparations for nutrition orenjoyment purposes. The preparations within the scope of the inventioncan also be in the form of capsules, tablets (uncoated and coatedtablets, e.g. enteric coatings), dragées, granules, pellets, solidsmixtures, dispersions in liquid phases, in the form of emulsions, in theform of powders, in the form of solutions, in the form of pastes, or inthe form of other preparations which can be swallowed or chewed, and inthe form of food supplements.

The preparations can also be in the form of capsules, tablets (uncoatedand coated tablets, e.g. enteric coatings), dragées, granules, pellets,solids mixtures, dispersions in liquid phases, in the form of emulsions,in the form of powders, in the form of solutions, in the form of pastes,or in the form of other preparations which can be swallowed or chewed,for example in the form of food supplements.

The semi-finished products are generally used for the production ofready-to-use or ready-to-eat preparations for nutrition or enjoymentpurposes.

Further constituents of a ready-to-eat preparation or semi-finishedproduct for nutrition or enjoyment purposes can be conventional basesubstances, auxiliary substances and additives for foods or enjoymentfoods, for example water, mixtures of fresh or processed, vegetable oranimal base or raw substances (e.g. raw, roast, dried, fermented, smokedand/or boiled meat, bone, cartilage, fish, vegetables, herbs, nuts,vegetable juices, vegetable pastes or mixtures thereof), digestible ornon-digestible carbohydrates (e.g. sucrose, maltose, fructose, glucose,dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose),sugar alcohols (e.g. sorbitol, erythritol), natural or hardened fats(e.g. tallow, lard, palm fat, cocoa fat, hardened vegetable fat), oils(e.g. sunflower oil, groundnut oil, maize germ oil, olive oil, fish oil,soya oil, sesame oil), fatty acids or their salts (e.g. potassiumstearate), proteinogenic or non-proteinogenic amino acids and relatedcompounds (e.g. γ-aminobutyric acid, taurine), peptides (e.g.glutathione), natural or processed proteins (e.g. gelatin), enzymes(e.g. peptidases), nucleic acids, nucleotides, taste correctors forunpleasant taste impressions, further taste modulators for further,generally not unpleasant taste impressions, other taste-modulatingsubstances (e.g. inositol phosphate, nucleotides such as guanosinemonophosphate, adenosine monophosphate or other substances such assodium glutamate or 2-phenoxypropionic acid), emulsifiers (e.g.lecithins, diacylglycerols, gum arabic), stabilisers (e.g. carrageenan,alginate), preservatives (e.g. benzoic acid and its salts, sorbic acidand its salts), antioxidants (e.g. tocopherol, ascorbic acid), chelators(e.g. citric acid), organic or inorganic acidifying agents (e.g. aceticacid, phosphoric acid), additional bitter substances (e.g. quinine,caffeine, limonene, amarogentine, humulone, lupulone, catechols,tannins), substances that prevent enzymatic browning (e.g. sulfite,ascorbic acid), ethereal oils, plant extracts, natural or syntheticcolourings or colouring pigments (e.g. carotinoids, flavonoids,anthocyans, chlorophyll and derivatives thereof), spices, trigeminallyactive substances or plant extracts containing such trigeminally activesubstances, synthetic, natural or nature-identical flavourings orodorants as well as odour correctors.

Food compositions according to the invention, for example those in theform of preparations or semi-finished products, preferably comprise aflavour composition in order to complete and refine the taste and/orodour. A preparation can comprise as constituents a solid carrier and aflavour composition. Suitable flavour compositions comprise, forexample, synthetic, natural or nature-identical flavourings, odorantsand taste-imparting substances, reaction flavourings, smoke flavouringsor other flavour-giving preparations (e.g. protein (partial)hydrolysates, preferably protein (partial) hydrolysates having a higharginine content, barbecue flavourings, plant extracts, spices, spicepreparations, vegetables and/or vegetable preparations) as well assuitable auxiliary substances and carriers. Particularly suitable hereare the flavour compositions or constituents thereof which produce aroasted, meaty (in particular chicken, fish, seafood, beef, pork, lamb,mutton, goat), vegetable-like (in particular tomato, onion, garlic,celery, leek, mushroom, aubergine, seaweed), spicy (in particular blackand white pepper, cardamom, nutmeg, pimento, mustard and mustardproducts), fried, yeast-like, boiled, fatty, salty and/or pungentflavour impression and accordingly can enhance the spicy impression. Theflavour compositions generally comprise more than one of the mentionedingredients.

The food compositions of the present invention are preferably selectedfrom the group comprising

-   -   confectionery, preferably reduced-calorie or calorie-free        confectionery, preferably selected from the group comprising        muesli bar products, fruit gums, dragées, hard caramels and        chewing gum,    -   non-alcoholic drinks, preferably selected from the group        comprising green tea, black tea, (green, black) tea drinks        enriched with (green, black) tea extracts, rooibos tea, other        herbal teas, fruit-containing low-sugar or sugar-free soft        drinks, isotonic drinks, nectars, fruit and vegetable juices,        fruit and vegetable juice preparations,    -   instant drinks, preferably selected from the group comprising        instant (green, black, rooibos, herbal) tea drinks,    -   cereal products, preferably selected from the group comprising        low-sugar and sugar-free breakfast cereals and muesli bars,    -   dairy products, preferably selected from the group comprising        reduced-fat and fat-free milk drinks, yoghurt, kefir, whey,        buttermilk and ice-cream,    -   products made from soy protein or other soybean fractions,        preferably selected from the group comprising soy milk, products        produced from soy milk, drinks containing isolated or        enzymatically treated soy protein, drinks containing soy flour,        preparations containing soy lecithin, products produced from        preparations containing soy lecithin and mixtures with fruit        preparations and optionally flavours,    -   sweetener preparations, tablets and sachets,    -   sugar-free dragées,    -   ice-cream, with or without milk-based constituents, preferably        sugar-free.

Aroma or Flavouring Compounds

Aroma compounds and flavouring agents (component d) are well known inthe art can be added to the flavour compositions of the invention. Theseflavouring agents can be chosen from synthetic flavouring liquid and/oroils derived from plants leaves, flowers, fruits and so forth, andcombinations thereof. Representative flavouring liquids include:artificial, natural or synthetic fruit flavours such as eucalyptus,lemon, orange, banana, grape, lime, apricot and grapefruit oils andfruit essences including apple, strawberry, cherry, orange, pineappleand so forth; bean and nut derived flavours such as coffee, cocoa, cola,peanut, almond and so forth; and root derived flavours such as licoriceor ginger.

The flavouring agent is preferably selected from the group consisting ofessential oils and extracts, tinctures and balsams, such as, forexample, anisole, basil oil, bergamot oil, bitter almond oil, camphoroil, citronella oil, lemon oil; Eucalyptus citriodora oil, eucalyptusoil, fennel oil, grapefruit oil, camomile oil, spearmint oil, carawayoil, lime oil, mandarin oil, nutmeg oil (in particular nutmeg blossomoil=maces oil, mace oil), myrrh oil, clove oil, clove blossom oil,orange oil, oregano oil, parsley (seed) oil, peppermint oil, rosemaryoil, sage oil (clary sage, Dalmatian or Spanish sage oil), star aniseedoil, thyme oil, vanilla extract, juniper oil (in particular juniperberry oil), wintergreen oil, cinnamon leaf oil; cinnamon bark oil, andfractions thereof, or constituents isolated therefrom.

It is of particular advantage if the flavoured composition according tothe invention comprises at least one flavouring agent, preferably two,three, four, five, six, seven, eight or more flavouring agents chosenfrom the following group: menthol (preferably I-menthol and/or racemicmenthol), anethole, anisole, anisaldehyde, anisyl alcohol, (racemic)neomenthol, eucalyptol (1,8-cineol), menthone (preferably L-menthone),isomenthone (preferably D-isomenthone), isopulegol, menthyl acetate(preferably L-menthyl acetate), menthyl propionate, carvone (preferably(−)-carvone, optionally as a constituent of a spearmint oil), methylsalicylate (optionally as a constituent of a wintergreen oil), eugenolacetate, isoeugenol methyl ether, beta-homocyclocitral, eugenol,isobutyraldehyde, 3-octanol, dimethyl sulfide, hexanol, hexanal,trans-2-hexenal, cis-3-hexenol, 4-terpineol, piperitone, linalool,8-ocimenyl acetate, isoamyl alcohol, isovaleraldehyde, alpha-pinene,beta-pinene, linnonene (preferably D-linnonene, optionally as aconstituent of an essential oil), piperitone, trans-sabinene hydrate,menthofuran, caryophyllene, germacrene D, cinnamaldehyde, mint lactone,thymol, gamma-octalactone, gamma-nonalactone, gamma-decalactone,(1,3E,5Z)-undecatriene, 2-butanone, ethyl formate, 3-octyl acetate,isoamyl isovalerate, cis- and trans-carvyl acetate, p-cymol,damascenone, damascone, cis-rose oxide, trans-rose oxide, fenchol,acetaldehyde diethyl acetal, 1-ethoxyethyl acetate, cis-4-heptenal,cis-jasmone, methyl dihydrojasmonate, 2′-hydroxypropiophenone, menthylmethyl ether, myrtenyl acetate, 2-phenylethyl alcohol, 2-phenylethylisobutyrate, 2-phenylethyl isovalerate, geraniol, nerol andviridiflorol.

In particular preferred aroma or flavouring compounds encompass menthol,cineol, eugenol, thymol, cinnamic aldehyde, peppermint oil, spearmintoil, eucalyptus oil, thyme oil, cinnamon oil, clove oil, spruce needleoil, fennel oil, sage oil, aniseed oil, star anise oil, chamomile oil,and caraway oil, and their mixtures.

Sweeteners

The term “sweeteners” here denotes substances having a relativesweetening power of at least 25, based on the sweetening power ofsucrose (which accordingly has a sweetening power of 1). Sweeteners tobe used in an orally consumable product (in particular foodstuff, feedor medicament) according to the invention (a) are preferablynon-cariogenic and/or have an energy content of not more than 5 kcal pergram of the orally consumable product.

Advantageous sweeteners in a preferred food composition according to theinvention are selected from the following groups:

Naturally occurring sweeteners, preferably selected from the groupcomprising

-   -   miraculin, monellin, mabinlin, thaumatin, curculin, brazzein,        pentaidin, D-phenylalanine, D-tryptophan, and extracts or        fractions obtained from natural sources, comprising those amino        acids and/or proteins, and the physiologically acceptable salts        of those amino acids and/or proteins, in particular the sodium,        potassium, calcium or ammonium salts;    -   neohesperidin dihydrochalcone, naringin dihydrochalcone,        stevioside, steviolbioside, rebaudiosides, in particular        rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D,        rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H,        dulcosides and rubusoside, suavioside A, suavioside B,        suavioside G, suavioside H, suavioside I, suavioside J,        baiyunoside 1, baiyunoside 2, phlomisoside 1, phlomisoside 2,        phlomisoside 3 and phlomisoside 4, abrusoside A, abrusoside B,        abrusoside C, abrusoside D, cyclocaryoside A and cyclocaryoside        I, osladin, polypodoside A, strogin 1, strogin 2, strogin 4,        selligueain A, dihydroquercetin 3-acetate, perillartin,        telosmoside A₁₅, periandrin I-V, pterocaryosides,        cyclocaryosides, mukuroziocides, trans-anethole,        trans-cinnamaldehyde, bryosides, bryonosides, bryonodulcosides,        carnosiflosides, scandenosides, gypenosides, trilobatin,        phloridzin, dihydroflavanols, hematoxylin, cyanin, chlorogenic        acid, albiziasaponin, telosmosides, gaudichaudioside,        mogrosides, mogroside V, hernandulcins, monatin, phyllodulcin,        glycyrrhetinic acid and derivatives thereof, in particular        glycosides thereof such as glycyrrhizine, and the        physiologically acceptable salts of those compounds, in        particular the sodium, potassium, calcium or ammonium salts;    -   extracts or concentrated fractions of the extracts, selected        from the group comprising thaumatococcus extracts (katamfe        plant), extracts from Stevia ssp. (in particular Stevia        rebaudiana), swingle extracts (Momordica or Siratia grosvenorii,        Luo-Han-Guo), extracts from Glycerrhyzia ssp. (in particular        Glycerrhyzia glabra), extracts from Rubus ssp. (in particular        Rubus suavissimus), citrus extracts and extracts from Lippia        dulcis;

Synthetic sweet-tasting substances, preferably selected from the groupcomprising magap, sodium cyclamate or other physiologically acceptablesalts of cyclamic acid, acesulfame K or other physiologically acceptablesalts of acesulfame, neohesperidin dihydrochalcone, naringindihydrochalcone, saccharin, saccharin sodium salt, aspartame,superaspartame, neotame, alitame, advantame, perillartin, sucralose,lugduname, carrelame, sucrononate and sucrooctate.

Thickeners

Advantageous thickeners in a preferred orally consumable product (inparticular foodstuff, feed or medicament) according to the invention areselected from the group comprising: crosslinked polyacrylic acids andderivatives thereof, polysaccharides and derivatives thereof, such asxanthan gum, agar-agar, alginates or tyloses, cellulose derivatives, forexample carboxymethylcellulose or hydroxycarboxymethylcellulose, fattyalcohols, monoglycerides and fatty acids, polyvinyl alcohol andpolyvinylpyrrolidone.

Preference is given according to the invention to an orally consumableproduct (in particular foodstuff or feed) which comprises milk thickenedwith lactic acid bacteria and/or cream thickened with lactic acidbacteria and which preferably is selected from the group comprisingyoghurt, kefir and quark.

A food composition according to the invention comprising milk thickenedwith lactic acid bacteria and/or cream thickened with lactic acidbacteria is advantageously an orally consumable product which comprisesa probiotic, wherein the probiotic is preferably selected from the groupcomprising Bifidobacterium animalis subsp. lactis BB-12, Bifidobacteriumanimalis subsp. lactis DN-173 010, Bifidobacterium animalis subsp.lactis HN019, Lactobacillus acidophilus LA5, Lactobacillus acidophilusNCFM, Lactobacillus johnsonii La1, Lactobacillus caseiimmunitass/defensis, Lactobacillus casei Shirota (DSM 20312),Lactobacillus casei CRL431, Lactobacillus reuteri (ATCC 55730) andLactobacillus rhamnosus (ATCC 53013).

Additives for Chewing Gums

Particular preference is given to an orally consumable product (inparticular foodstuff, feed or medicament) according to the inventionthat is a chewing gum and comprises a chewing-gum base. The chewing-gumbase is preferably selected from the group comprising chewing-gum orbubble-gum bases. The latter are softer, so that gum bubbles can also beformed therewith. Preferred chewing-gum bases according to the inventioninclude, in addition to the natural resins or the natural latex chiclethat are traditionally used, elastomers such as polyvinyl acetate (PVA),polyethylene, (low or medium molecular weight) polyisobutene (PIB),polybutadiene, isobutene-isoprene copolymers (butyl rubber),polyvinyethyl ether (PVE), polyvinylbutyl ether, copolymers of vinylesters and vinyl ethers, styrene-butadiene copolymers (styrene-butadienerubber, SBR) or vinyl elastomers, for example based on vinylacetate/vinyl laurate, vinyl acetate/vinyl stearate or ethylene/vinylacetate, as well as mixtures of the mentioned elastomers, as described,for example, in EP 0 242 325, U.S. Pat. Nos. 4,518,615, 5,093,136,5,266,336, 5,601,858 or 6,986,709. In addition, chewing-gum bases thatare preferably to be used according to the invention preferably comprisefurther constituents such as, for example, (mineral) fillers,plasticisers, emulsifiers, antioxidants, waxes, fats or fatty oils, suchas, for example, hardened (hydrogenated) vegetable or animal fats,mono-, di- or tri-glycerides. Suitable (mineral) fillers are, forexample, calcium carbonate, titanium dioxide, silicon dioxide, talcum,aluminium oxide, dicalcium phosphate, tricalcium phosphate, magnesiumhydroxide and mixtures thereof. Suitable plasticisers, or agents forpreventing adhesion (detackifiers), are, for example, lanolin, stearicacid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate),triacetin (glycerol triacetate), triethyl citrate. Suitable waxes are,for example, paraffin waxes, candelilla wax, carnauba wax,microcrystalline waxes and polyethylene waxes. Suitable emulsifiers are,for example, phosphatides such as lecithin, mono- and di-glycerides offatty acids, for example glycerol monostearate.

Chewing gums according to the invention (in particular as disclosedabove) preferably comprise constituents such as sugars of differenttypes, sugar substitutes, other sweet-tasting substances, sugar alcohols(in particular sorbitol, xylitol, mannitol), ingredients having acooling effect, taste correctors for unpleasant taste impressions,further taste-modulating substances (e.g. inositol phosphate,nucleotides such as guanosine monophosphate, adenosine monophosphate orother substances such as sodium glutamate or 2-phenoxypropionic acid),humectants, thickeners, emulsifiers, stabilisers, odour correctors andflavours (e.g. eucalyptus-menthol, cherry, strawberry, grapefruit,vanilla, banana, citrus, peach, blackcurrant, tropical fruits, ginger,coffee, cinnamon, combinations (of the mentioned flavours) with mintflavours as well as spearmint and peppermint on their own). Thecombination inter alia of the flavours with further substances that havecooling, warming and/or mouth-watering properties is of particularinterest.

Methods for Stabilizing the Taste and/or Odor of Fatty Acid (Esters)

Another object of the present invention is to provide a method forstabilizing the taste and/or odor of unsaturated fatty acids (esters),whereby acetophenone derivative of formula (I)

-   -   wherein    -   R₁ stands for hydrogen or methyl, and    -   R₂ stands for hydrogen, hydroxyl or a —OCH₃ group, or a        cosmetically or pharmaceutically acceptable salt thereof,        is added into the unsaturated fatty acids (esters).

Preferably, the acetophenone derivative of formula (I) are selected fromthe group consisting of

or their mixtures. More preferably the acetophenone derivative offormula (I) is 4-hydroxyacetophenone.

In a preferred embodiment the unsaturated fatty acids (esters) are mono-or polyunsaturated C₈-C₂₂ fatty acids or its monohydric or polyhydricC₁-C₁₈ aliphatic alcohols ester.

In a more preferred embodiment the mono- or polyunsaturated C₈-C₂₂ fattyacids or its monohydric or polyhydric C₁-C₁₈ aliphatic alcohols estercomprise:

(b-1) at least one acyl compound of formula (II)

-   -   wherein    -   R stands for hydrogen atom or an C₁-C₁₈ alkyl group and    -   X represents a mono- or polyunsaturated C₈-C₂₂ acyl group,        and/or        (b-2) at least one acylglycerol compound of formula (III)

-   -   wherein    -   X′, X″ and X″′ independently of one another represents a        hydrogen atom or a saturated or mono- or polyunsaturated C₈-C₂₂        acyl group,    -   with the proviso that X′, X″ and X″′ do not simultaneously        represent hydrogen atom and at least one of X′, X″ and X″′ being        unsaturated acyl group.

In a another preferred embodiment the added amount of acetophenonederivative of formula (I) is in the range from about 0.01 to 5 wt. %,preferably in the range from 0.05 to 2 wt. %, and particularlypreferably in the range from 0.1 to 1 wt. % relative to the total weightof the composition.

EXAMPLES Example 1 Evaluation of Anti-Oxidant Activity

By means of the ABTS-assay the anti-oxidative capacity of4-hydroxyacetophenone and alpha-tocopherol was compared. 2,2′-azinobis-(3-ethylbenzothiazoline 6-sulfonic acid) (ABTS) was transformed bypotassium persulfate into the blue-green radical cation ABTS•⁺. Throughthe addition of 4-hydroxyacetophenone and alpha-tocopherol the radicalcations were reduced and discoloration was observed, which wasdetermined photometrically by Absorption at 734 nm. The inhibition ofthe radical formation of the test substance is calculated by thefollowing formula:

${{Inhibition}\mspace{14mu}\lbrack\%\rbrack} = {100 - \left( {\frac{A_{{test}\mspace{14mu} {substance}}}{A_{control}} \times 100} \right)}$

Wherein the abbreviations have the following meanings:

-   -   A_(test substance): Absorption of the wells with test substance        including 4-hydroxyacetophenone and alpha-tocopherol    -   A_(control): Absorption of the wells without test substance

From the inhibition of the radical formation [%] in a series ofdilutions of tested samples the IC₅₀ was calculated. This is theconcentration at which the radical formation is inhibited by 50%. Theresults are shown in Table 1:

TABLE 1 Activity based on the inhibition of radical formation (meanvalue from at least 2 independent tests) Test Substance IC₅₀ (μM)4-hydroxyacetophenone 262.3 alpha-tocopherol 26.8

The results show that 4-hydroxyacetophenone exhibits a 10 fold higherIC₅₀ value than alpha-tocopherol. That means 4-hydroxyacetophenone witha concentration of 262.3 μM can inhibit 50% of the radical formation,whereas only 26.8 μM of alpha-tocopherol were required to do the same.Therefore 4-hydroxyacetophenone has much weaker antioxidant activitycompared with alpha-tocopherol.

Example 2 Stabilization of Argan Oil

To evaluate the odor protecting effect of Hydroxyacetophenone on oils,oil samples comprising Argan oil without (A) and with differentadditives (B to E) were prepared as given in Table 2.

TABLE 2 The composition of oil samples A to E (amounts in % b.w.)Ingredient INCI Name A B C D E Argan oil Argania Spinosa Kernel Oil Ad100 Ad 100 Ad 100 Ad 100 Ad 100 Alpha-Tocopherol Tocopherol \ 0.5 \ \ \Tocopheryl acetate Tocopheryl acetate \ \ 0.5 \ \ Covi-Ox T 70CTocopherol \ \ \ 0.5 \ (blend of tocopherols) 4-HydroxyacetophenoneHydroxyacetophenone \ \ \ \ 0.5

Generally argan oil (INCI: Argania Spinosa Kernel Oil) is a clear,yellow to orange liquid characterized by acylglycerols containing 42-50%oleic acid (C18:1), 30-36% linoleic acid, 12-16% palmitic acid (C16:0),and 4-6% stearic acid (C18:0). It has a very characteristic and strongodour.

In this experiment the Argan oil quality used was characterized byacylglycerol compounds containing 51% oleic acid (C18:1), 35% linoleicacid, 14% palmitic acid (C16:0), and 6% stearic acid (C18:0) asdetermined by GC analysis after methanolysis via the respective fattyacid methyl esters. Furthermore, it contained 0.29% oleic acid (C18:1)and 0.25% linoleic acid as free fatty acids as determined by HPLCanalysis with light scattering detection and diode array detection,respectively.

Acyl and acylglycerol compounds were characterized by HPLC-MS and listedin Table 3: HPLC-MS: YMC ODS-AQ, 5 μm, 150×3 mm with pre-column,temperature: 40° C., flow: 0.4 ml/min, gradient from 100% methanol to100% isopropanol, detection wavelength 205 nm, after column addition ofa 100 mM methanolic ammonium formiate solution by syringe pump, flow:0.150 μl/h, MS ion trap, ESI in positive and negative ion mode with AutoMS/MS fragmentation, scan 200 to 1500.

TABLE 3 Characterization of acyl and acylglycerol compounds by HPLC-MSmeasurement in negative (investigation of free fatty acids) and positive(investigation of acylglycerol compounds) ion mode Retention ESI ESIMolecular time in min neg. m/z pos m/z weight M Compound 3.2 279 (1) 280Linoleic acid 3.5 255 (1) 256 Palmitic acid 3.6 281 (1) 282 Oleic acid4.1 283 (1) 284 Stearic acid 2.9 377 (3) 354 L Monoacylglycerol 3.2 379(3) 356 O Monoacylglycerol 6.7 639 (2) 621 LS Diacylgylcerol 6.9 635 (2)617 LL Diacylgylcerol 7.3 615 (2) 597 PS Diacylgylcerol 7.4 611 (2) 593LP Diacylgylcerol 7.7 637 (2) 619 OL Diacylgylcerol 7.7 641 (2) 623 OSDiacylglycerol 8.4 613 (2) 595 OP Diacylglycerol 8.5 639 (2) 621 OODiacylgylcerol 14.4 897 (2) 879 LLL Triacylglycerol 15.2 873 (2) 855 LLPTriacylglycerol 15.3 899 (2) 881 LLO Triacylglycerol 15.6 825 (2) 807PPP Triacylglycerol 15.7 849 (2) 831 PPL Triacylglycerol 15.9 875 (2)857 OLP Triacylglycerol 16.2 901 (2) 883 LLS Triacylglycerol 16.2 901(2) 883 OOL Triacylglycerol 16.5 851 (2) 833 PPO Triacylglycerol 16.6877 (2) 859 OOP Triacylglycerol 16.9 903 (2) 885 OOO Triacylglycerol17.5 881 (2) 863 SSP Triacylglycerol 17.5 879 (2) 861 OPSTriacylglycerol 17.6 905 (2) 887 OOS Triacylglycerol (1) M − 1 for the[M − H]⁻ ion (2) M + 18 for the [M + NH₄]⁺ ion (3) M + 23 for the [M +Na]⁺ ion In the table acyl radicals are abbreviated as follows: O =oleic acid, L = linoleic acid, P = palmitic acid, and S = stearic acid.

The oil samples were divided respectively into 3 portions each and theportions were stored for 1 and 2 months either at room temperatureexposed to normal daylight (RTL) or at 40° C. or 50° C. in a heatingcabinet, respectively. After the treatments, the absorbance at 232 nmwas determined as this correlates with the state of oxidation bydetecting conjugated dienes as specific oxidized compounds. Modulationversus start t=0 was calculated by the following formula and listed inTable 4:

${{Modulation}\mspace{14mu}\lbrack\%\rbrack} = \left( {\frac{{{{Absorbance}\mspace{14mu} {after}\mspace{14mu} {treatment}} - {{Absorbance}\mspace{14mu} {at}\mspace{14mu} t}} = 0}{{{Absorbance}\mspace{14mu} {at}\mspace{14mu} t} = 0} \times 100} \right)$

TABLE 4 Absorbance at 232 nm and Modulation versus t = 0 A B C D EAbsorbance at 232 nm Start t = 0 0.1581 0.2655 0.2101 0.2149 0.2590 RTL,1 month 0.4993 0.8717 0.4422 0.5530 0.5260 RTL, 2 months 0.9468 1.90030.9839 1.1014 1.2119 40° C., 1 month 0.2100 0.9206 0.2885 0.3747 0.346740° C., 2 months 0.3195 1.9008 0.4536 0.6761 0.4352 50° C., 1 month0.3749 0.8642 0.4640 0.7117 0.4860 50° C., 2 months 0.8220 3.9160 0.95931.7329 0.8895 Modulation versus t = 0 [%] RTL, 1 month 216 228 110 157103 RTL, 2 months 499 616 368 413 368 40° C., 1 month 33 247 37 74 3440° C., 2 months 102 616 116 215 68 50° C., 1 month 137 225 121 231 8850° C., 2 months 420 1375 357 706 243

As can be seen from the able, 0.5% of 4-hydroxyacetophenone (sample E)leads to a lower increase of absorbance at 232 nm compared to sample A(Argan oil without additive) after 1 and 2 months. The protective effectof 4-hydroxyacetophenone was observed at all 3 treatments. 0.5%4-hydroxyacetophenone (sample E) exhibited a better protection than 0.5%alpha-tocopherol (sample B), 0.5% tocopheryl acetate (sample C) and 0.5%Covi-Ox T 70C which is a blend of tocopherols (sample D).

Example 3 Stabilization of Avocado Oil

To evaluate the odour protecting effect of Hydroxyacetophenone on oils,oil samples comprising avocado oil without (A) and with differentadditives (B to D) were prepared as given in Table 5.

TABLE 5 The composition of oil samples A to D (amounts in % b.w.)Ingredient INCI Name A B C D Avocado oil Persea Ad 100 Ad 100 Ad 100 Ad100 Gratissima Oil Alpha- Tocopherol \ 0.5 \ \ Tocopherol TocopherylTocopheryl \ \ 0.5 \ Acetate Acetate 4-Hydroxy- Hydroxyaceto- \ \ \ 0.5acetophenone phenone

Generally avocado oil (INCI: Persea Gratissima Oil) is clear or cloudy,colorless to yellow-green liquid characterized by acylglycerolscontaining about 65% oleic acid (C18:1) and 6-10% linoleic acid (C18:2)(Ölpflanzen-Pflanzenöle, L. Roth and K. Kormann ecomed 2000, page 117).

The avocado oil quality used in this experiment was characterized byacylglycerols containing 63% oleic acid (C18:1), 21% palmitic acid(C16:0), 11% linoleic acid, and 10% palmitoleic acid (C16:1) asdetermined by GC analysis after methanolysis via the respective fattyacid methyl esters.

Acyl and acylglycerol compounds were characterized by HPLC-MS and listedin Table 6: HPLC-MS: YMC ODS-AQ, 5 μm, 150×3 mm with pre-column,temperature: 40° C., flow: 0.4 ml/min, gradient from 100% methanol to100% isopropanol, detection wavelength 205 nm, after column addition ofa 100 mM methanolic ammonium formiate solution by syringe pump, flow:0.150 μl/h, MS ion trap, ESI in positive and negative ion mode with AutoMS/MS fragmentation, Scan 200 to 1500.

TABLE 6 Characterization of acyl and acylglycerol compounds by HPLC-MSmeasurement in negative (investigation of free fatty acids) and positive(investigation of acylglycerol compounds) ion mode Retention ESI ESIMolecular time in min neg. m/z pos m/z weight M Compound 3.2 253 (1) 254Palmitoleic acid 3.3 279 (1) 280 Linoleic acid 3.5 255 (1) 256 Palmiticacid 3.6 281 (1) 282 Oleic acid 2.9 377 (3) 354 L Monoacylglycerol 3.0353 (3) 330 P Monoacylglycerol 3.2 379 (3) 356 O Monoacylglycerol 6.2587 (2) 569 PP Diacylgylcerol 6.3 583 (2) 565 pp Diacylgylcerol 6.5 609(2) 591 Lp Diacylgylcerol 6.8 635 (2) 617 LL Diacylgylcerol 7.3 585 567Pp Diacylglycerol 7.4 611 (2) 593 LP Diacylgylcerol 7.7 637 (2) 619 OLDiacylgylcerol 8.2 613 (2) 613 OP Diacylglycerol 8.5 639 (2) 621 OODiacylgylcerol 13.7 819 (2) 801 ppp Triacylglycerol 14.0 845 (2) 827 LppTriacylglycerol 14.3 871 (2) 853 LLp Triacylglycerol 14.5 897 (2) 879LLL Triacylglycerol 14.7 821 (2) 803 Ppp Triacylglycerol 15.1 873 (2)855 LLP Triacylglycerol 15.3 899 (2) 881 LLO Triacylglycerol 15.7 849(2) 831 PPL Triacylglycerol 15.9 875 (2) 857 OOp Triacylglycerol 16.1901 (2) 883 OOL Triacylglycerol 16.5 851 (2) 833 PPO Triacylglycerol16.7 877 (2) 859 OOP Triacylglycerol 17.0 903 (2) 885 OOOTriacylglycerol (1) M − 1 for the [M − H]⁻ ion (2) M + 18 for the [M +NH₄]⁺ ion (3) M + 23 for the [M + Na]⁺ ion In the table acyl radicalsare abbreviated as follows: O = oleic acid, L = linoleic acid, P =palmitic acid, and p = palmitoleic acid.

The oil samples were divided into 3 portions each and the portions werestored for 1 and 2 months either at room temperature exposed to normaldaylight (RTL) or at 40° C. or 50° C. in a heating cabinet,respectively. After the treatments, the absorbance at 232 nm wasdetermined as this correlates with the state of oxidation by detectingconjugated dienes as specific oxidized compounds. Modulation versusstart t=0 was calculated by the following formula and listed in Table 7:

${{Modulation}\mspace{14mu}\lbrack\%\rbrack} = \left( {\frac{{{{Absorbance}\mspace{14mu} {after}\mspace{14mu} {treatment}} - {{Absorbance}\mspace{14mu} {at}\mspace{14mu} t}} = 0}{{{Absorbance}\mspace{14mu} {at}\mspace{14mu} t} = 0} \times 100} \right)$

TABLE 7 Absorbance at 232 nm and Modulation versus t = 0 A B C DAbsorbance at 232 nm Start t = 0 0.4630 0.5207 0.5912 0.5773 RTL, 1month 0.9078 0.9457 0.7728 0.8978 RTL, 2 months 1.3464 1.5038 1.41121.3557 40° C., 1 month 0.8092 0.9207 0.7990 0.9151 40° C., 2 months1.1648 1.4635 1.5189 1.3776 50° C., 1 month 0.7653 1.0706 1.3888 0.831150° C., 2 months 1.1082 1.8845 1.5483 1.1739 Modulation versus t = 0 [%]RTL, 1 month 96 82 31 56 RTL, 2 months 191 189 139 135 40° C., 1 month75 77 35 59 40° C., 2 months 152 181 157 139 50° C., 1 month 65 106 13544 50° C., 2 months 139 262 162 103

As can be seen from the table, 0.5% of 4-hydroxyacetophenone (sample D)leads to a lower increase of absorbance at 232 nm compared to avocadooil without additive (A). The protective effect of 0.5% of4-hydroxyacetophenone was observed at all 3 treatments. 0.5% of4-hydroxyacetophenone (D) exhibited a better protection than 0.5%alpha-tocopherol (sample B) and 0.5% tocopheryl acetate (sample C).

Example 4 Olfactory Evaluation of a Crème Gel for Face Care Rich inLinoleic Acid

Two crème gels rich in linoleic acid with the compositions listed inTable 8 was prepared according to the following instructions:

-   (1) Firstly blending ingredients of phase A and phase B    respectively,-   (2) Dispersing ingredients of phase C into the mixture of phase B    and further adding ingredients of phase A under high shear,-   (3) Finally adding phase D under high shear into the mixture of    phase A, B and C.    The pH values of the obtained two crème gel samples are both 6.

TABLE 8 The Composition of crème gels A and B (amounts in % b.w.) PhaseIngredient INCI Name Gel A Gel B A Water Aqua Ad 100 Ad 100 GlycerinGlycerin 3.0 3.0 B Dracorin GOC Glyceryl Oleate Citrate 0.3 0.3Caprylic/Capric Triglyceride Linoleic acid Linoleic acid 12.0 12.0 SheaButter Butyrospermum Parkii Butter 2.0 2.0 4-Hydroxy-Hydroxyacetophenone 0.5 \ acetophenone C Cosmedia SP Sodium Polyacrylate1.2 1.2 D SymOcide PS Phenoxyethanol, Decylene 1.0 1.0 Glycol,1,2-Hexanediol E Tapioca Pure Tapioca Starch 1.0 1.0 Total= 100 100

According to GC analysis the used linoleic acid consisted of 67.96%linoleic acid (C18:2) and 25.92% oleic acid (C18:1).

The crème gel samples with and without 4-hydroxyacetophenone were codedA and B respectively. They were both divided into 2 parts. One part ofeach crème gel was kept at room temperature (RT) protected from light(Gel A1 and B1), the other part was exposed to 5 bar oxygen for 72 h at60° C. using the Oxypress device from Mikrolab Aarhus (Gel A2 and B2).After the oxygen treatment, the crème gels A2, B2 and B1 were evaluatedin direct comparison by 20 panellists. For olfactory evaluation,panellists were asked to rank the 3 samples according to their rancidsmell with 1=the most rancid and 3=the least rancid off-odour. Resultsof the evaluation are given in the following Table 9:

TABLE 9 Results from olfactory evaluation Number (percentage) ofvolunteers giving the score for the sample A2 (0.5% 4- B1 hydroxy- B2(Placebo) acetophenone) (Placebo) RT protected Score Oxypress Oxypressfrom light 1 (most rancid) 6 (30%) 14 (70%) 0 (0%) 2 9 (45%)  6 (30%)  5(25%) 3 (least rancid) 5 (25%) 0 (0%) 15 (75%)

The results clearly prove the odour stabilizing efficacy of4-hydroxyacetophenone: In comparison with placebo B1, which was storedat RT protected from light, 70% of the volunteers ranked the Oxypresstreated placebo B2 as the most rancid. Through the utilization of4-hydroxyacetophenone in the crème gel the obtained Gel A2 shows anobviously improved odour stability under the same Oxypress condition asplacebo B2, and 45% of the volunteers scored sample A2 with score 2 and25% with 3 (least rancid).

It can be undoubtedly concluded that the odour stability of the crèmegel rich in linoleic acid can be significantly improved by theapplication of 4-hydroxyacetophenone according to the present invention.

Example 5 Cosmetic Formulation Examples

Table 10a and 10b present a number of formulations according to theinvention

-   1=Anti-Aging Face Oil-   2=Glittering Dry Oil for Body & Hair-   3=Sublimating Hair Oil-   4=BB Cream SPF 15-   5=Baby Nappy Rash Cream—W/O-   6=Soft renewal body wash scrub-   7=Hair Butter-   8=Lipstick-   9=Lip Cream-   10=Concealer Stick-   11=Daily face cream SPF 20-   12=Cream Shower Oil-   13=Facial Cleansing gel-   14=Mascara-   15=Shampoo-   16=Massage Cream-   17=Bath oil-   18=Skin lightening cream-   19=Face gel-   20=O/W Soaking lotion for baby care wet wipes-   21=Anti-aging crème-   22=APD Roll-on Emulsion

TABLE 10a Cosmetic formulations (amounts in % b.w.) Ingredients 1 2 3 45 6 7 8 9 10 11 4-Hydroxyacetophenone 0.3 0.5 0.5 1 0.5 (SymSave H)Hydroxyacetophenone SymSave DH 1 1 0.8 Pentylene Glycol,Hydroxyacetophenone, 1,2- Hexanediol, Caprylyl Glycol SymOcide PH 1 1 1Phenoxyethanol, Hydroxyacetophenone, Caprylyl Glycol, Water (Aqua)Actipone Laminaria 2 Saccharina Glycerin, Aqua, Laminaria SaccharinaExtract Actipone Hortensia Root GW 1 Aqua, Glycerin, HydrangeaArborescens Root Extract Andiroba oil 1 2 Carapa Guaianensis Seed OilApricot seed oil 3.5 3 Prunus Armeniaca (Apricot) Kernel Oil Argan oil 49 0.5 Argania Spinosa Kernel Oil Ascorbyl Palmitate 0.1 AscorbylPalmitate Avocado oil 8 2 2 Persea Gratissima (Avocado) Oil Beeswax 10 5Cera Alba Bentone Gel GTCC V 2 Caprylic/Capric Triglyceride,Stearalkonium Hectorite, Propylene Carbonate Biotive L-Arginine 0.2Arginine Black currant oil 2 Ribes Nigrum (Black Currant) Seed OilBorage oil 3 Borago Officinalis Seed Oil Brazilian nut oil 3Bertholletia Excelsa Seed Oil Buriti oil 1 1 Mauritia Flexuosa Fruit OilCalendula oil 2 Glycine Soja (Soybean) Oil, Calendula Officinalis FlowerExtract Candelilla Wax Euphorbia Cera (Candelilla) 6 3 15 Wax CarbopolUltrez 21 0.2 1.1 Acrylates/C10-30 Alkyl Acrylate Crosspolymer CarnaubaWax 2 5 Cera Carnaubae depurata Cera Bellina 3 Polyglyceryl-3 BeeswaxCeramideBio Cetylhydroxyproline 0.5 Palmitamide Ceteareth-20 1.5Ceteareth-20 Cetiol CC 10 8 Dicaprylyl Carbonate Cetiol OE 12 10Dicaprylyl Ether Citric acid (sol. 20%) 7.1 0.2 Citric Acid Cocoa butter0.5 2 Theobroma Cacao (Cocoa) Seed Butter Coconut oil 12 Ad 100 3 CocosNucifera (Coconut) Oil Colorona Bordeaux 7.5 Mica, CI 77491 (1:1)Controx Ks 0.3 Tocopherol, Hydrogenated Palm Glyceride Citrate Corn oil5 Zea Mays (Corn) Oil Cosmetic color Brown 1 Powder CI 77891, CI 77492,CI 77491, CI 77499 Covapate Uniblue LC 6721 0.1 Ricinus Communis(Castor) Seed Oil 53-65%, CI 42090 (Blue 1 Lake) 35-47% Covapate UniredLC 3779 2 Ricinus Communis (Castor) Seed Oil 73-85%, CI 15850 15- 27%(Red no. 7) Covasilic 15 3 Silica Dimethyl Silylate Crodasinic LS-30 3.5Sodium Lauroyl Sarcosinate Cupuaçu butter 1 2 Theobroma GrandiflorumSeed Butter Cutina HR Powder 1.5 Hydrogenated Castor Oil CWD 8906 Wax 4Hydrogenated Vegetable Oil, CI 77891 (Titanium Dioxide) DC 2-8566 AminoFluid 1.5 Amodimethicone DC 2502 Fluid 5 Cetyl Dimethicone DC 345 Fluid5 Cyclomethicone DC 556 Fluid 1.5 4 Phenyl Trimethicone DC 593 4Dimethicone, Trimethylsiloxysilicate Dehymuls PGPH 5 Polyglyceryl-2Dipolyhydroxystearate Dimethicone 0.5 Dimethicone Disodium EDTA 0.1 0.10.1 Disodium EDTA Dracorin CE 3 Glyceryl Stearate Citrate Dracorin GOC 2Glyceryl Oleate Citrate, Caprylic/Capric Triglyceride Dragosantol 1000.1 Bisabolol Dragosine 0.1 Carnosine Dragoxat 89 10 3 10 5 EthylhexylIsononanoate Emulsiphos 2 2 Potassium Cetyl Phosphate, Hydrogenated PalmGlycerides Eutanol G 5 Octyldodecanol Evening primrose oil 2 OenotheraBiennis (Evening Primrose) Oil Extrapone Corail 1 Glycerin, Aqua,Hydrolyzed Corallina Officinalis Extrapone Lotus Flower 1 Aqua, ButyleneGlycol, Nelumbo Nucifera Flower Extract Extrapone Seaweed 1 Aqua,Butylene Glycol, Fucus Vesiculosus Extract Food color Iron oxide Yellow0.1 E172 CI 77492 Food color Titanium Dioxide 0.2 Powder E171 CI 77891Fragrance 1 1.1 0.7 1.5 0.3 0.5 Parfum Frescolat Plus 0.5 Menthol,Menthyl Lactate Frescolat X-Cool 0.3 Menthyl Ethylamido Oxalate Glycerin3 5 3 Glycerin Grape seed oil Ad 100 16 2 Vitis Vinifera (Grape) SeedOil Green Pigment 0.85 CI 77288, Triethoxycaprylylsilane Hemp oil 2Cannabis Sativa Seed Oil Hydrolite-5 2 3 Pentylene Glycol Hydromoist O 2Water (Aqua), Avena Sativa (Oat) Peptide Hydroviton Plus 3.0 Water(aqua), Pentylene Glycol, Glycerin, Fructose, Urea, Citric acid, SodiumHydroxide, Maltose, Sodium PCA, Sodium Chloride, Sodium Lactate,Trehalose, Allantoin, Sodium Hyaluronate, Glucose Isoadipate 12.7 5Diisopropyl Adipate Isodragol 3 5 5 8 Triisononanoin Jojoba oil 10 172.5 5 5 Simmondsia Chinensis (Jojoba) Seed Oil Jojoba Wax Flakes 1Hydrogenated Jojoba Oil Keltrol CG-T 0.3 0.2 0.1 Xanthan Gum Lanette O 13 5 Cetearyl Alcohol Lanette 16 1 1 Cetyl Alcohol Lanette 22 1 BehenylAlcohol Linseed oil 2 Linum Usitatissimum (Linseed) Seed Oil Lipo Luffa30/100 1 Luffa Cylindrica Fruit Lotus Exfoliator 500 0.3 NelumboNucifera Seed Powder Macadamia oil 2 3 4 Macadamia Ternifolia Seed OilMagnesium Sulfate Hepta 0.5 Hydrate Magnesium Sulfate Micropoly 250S 0.7Polyethylene Monomuls 90-O18 1 Glyceryl Oleate Murumuru butter 2 4.5Astrocaryum Murumuru Seed Butter Neo Heliopan 357 3.3 3 ButylMethoxydibenzoylmethane Neo Heliopan 303 8 Octocrylene Neo Heliopan HMS5 10 Homosalate Neo Heliopan Hydro used as 8 a 25% aq. Solutionneutralized by arginine Phenylbenzimidazole Sulfonic Acid Neo HeliopanOS 5 Ethylhexyl Salicylate Neutral oil Ad 100 3 8 8 Caprylic/caprictriglyceride Olive oil 9 Olea Europaea (Olive) Fruit Oil Orgasol Caresse1 Polyamide-5 Ozokerite Wax 1899 2 Ozokerite Panthenol 0.5 PanthenolPassion fruit oil 3 1 2 Passiflora Edulis Seed Oil PCL Liquid 5 CetearylEthylhexanoate, Isopropyl Myristate PCL Liquid 100 5 CetearylEthylhexanoate PCL Solid 3 Stearyl Heptanoate, Stearyl Caprylate Peanutoil 2 Arachis Hypogaea (Peanut) Oil Perfume oil PFO1 1.2 0.1 Perfume oilPFO2 0.6 Phytoconcentrole Camomile 1 Bisabolol, Caprylic/CapricTriglyceride, Chamomilla Recutita Flower Extract Phytoconcentrole Cotton2 Glycine Soja (Soybean) Oil, Gossypium Herbaceum (Cotton) Seed OilPomgranate seed oil 2 2 Punica Granatum (Pomegranate) Seed Oil Poppy oil1 Papaver Orientale (Poppy) Seed Oil Potassium Sorbate 0.3 PotassiumSorbate Protelan AGL 8 Sodium Lauroyl Glutamate Proteol APL 2 SodiumCocoyl Apple Amino Acids Pumpkin seed oil 5 Cucurbita Pepo (Pumpkin)Seed Oil PVP K-90 2 PVP Ronaflair M-Sphere 7.5 Mica (CI 77019) 99%,Silica 1% Ricinus Oil, pharm. raff Ad 100 Ricinus Communis (Castor) SeedOil Safflower oil 5 3 Carthamus Tinctorius (Safflower) Seed Oil Sesameoil 1 3 Sesamum Indicum (Sesame) Seed Oil Shea butter 2.5 Ad 100 3Butyrospermum Parkii (Shea) Butter Simugel EG 1 Sodium Acrylate/SodiumAcryloyldimethyl Taurate Copolymer, Isohexadecane, Polysorbate 80 SodiumHydroxide, 10% 0.3 2.1 solution Aqua, Sodium Hydroxide Soybean oil 7Glycine Soja (Soybean) Oil Stearic acid 5 Stearic Acid Sunflower oil 12Helianthus Annuus (Sunflower) Seed Oil Sunshine Crystal Bronze 0.2Synthetic Fluorphlogopite CI 77491 Sunshine Crystal Golden 0.4 SyntheticFluorphlogopite CI 77891 CI 77491 Sweet almond oil 5 14 7 3 PrunusAmygdalus Dulcis (Sweet Almond) Oil Sym3D 0.25 HydroxymethoxyphenylPropylmethylmethoxybenzofuran SymBronze 2 Caprylic/Capric Triglyceride,Isochrysis Galbana Extract SymCalmin 1 Butylene Glycol, PentyleneGlycol, Hydroxyphenyl Propamidobenzoic Acid SymCare O 2 Hexyldecanol,Pentylene Glycol, 4-t- Butylcyclohexanol, Bisabolol, CetylhydroxyprolinePalmitamide, Hydroxyphenyl Propamidobenzoic Acid, Stearic Acid, BrassicaCampestris (Rapeseed) Sterols, Zingiber Officinale (Ginger) Root ExtractSymClariol 0.3 Decylene Glycol SymFinity 1298 0.1 Echinacea PurpureaExtract SymGlucan 1 Aqua, Glycerin, Beta-Glucan SymMatrix 0.1Maltodextrin, Rubus Fructicosus (Blackberry) Leaf Extract SymMollient S5 5 Cetearyl Nonanoate SymRelief 100 0.2 Bisabolol, Zingiber Officinale(Ginger) Root Extract SymRepair 100 2 Hexyldecanol, Bisabolol,Cetylhydroxyproline Palmitamide, Stearic Acid, Brassica Campestris(Rapeseed) Sterols SymSitive 1609 1 Pentylene Glycol, 4-t-Butylcyclohexanol Tamanu oil 0.2 Calophyllum Inophyllum Seed OilTegosoft TN 4 C12-15 Alkyl Benzoate Tetrasodium EDTA 0.1 TetrasodiumEDTA Titan dioxide 4 Titan dioxide Tocopherol 0.1 Tocopherol Tocopherylacetate 0.5 Tocopheryl acetate Triethanolamine 99% 2.5 TriethanolamineViamerine WH 60 1 Hydroxystearic/Linolenic/ Oleic Polyglycerides VitaminF Ethyl Ester 1 Ethyl Linoleate, Ethyl Linolenate, Ethyl Oleate Water Ad100 Ad 100 Ad 100 Ad 100 Ad 100 Ad 100 Aqua Wheat germ oil 2 TriticumVulgare (Wheat) Germ Oil White pigment 7 CI 77891, Ricinus (Castor) seedoil Yellow pigment 0.15 CI 77492, Triethoxycaprylylsilane Zinc oxide 10Zinc oxide

TABLE 10b Cosmetic formulations (amounts in % b.w.) Ingredients 12 13 1415 16 17 18 19 20 21 22 4-Hydroxyacetophenone 0.5 0.5 0.2 0.3 0.5 0.50.2 (SymSave H) Hydroxyacetophenone SymSave DH 1 1 Pentylene Glycol,Hydroxyacetophenone, 1,2- Hexanediol, Caprylyl Glycol SymOcide PH 1 1Phenoxyethanol, Hydroxyacetophenone, Caprylyl Glycol, Water (Aqua)Actipone Ginger Juice 1 (Organic) GW Glycerin, Zingiber Officinale(Ginger) Root Juice, Water (Aqua) Andiroba oil 1 Carapa Guaianensis SeedOil Antil 127 q.s. PEG-120 Methyl Glucose Dioleate Apricot seed oil 0.5Prunus Armeniaca (Apricot) Kernel Oil Argan oil 5 Argania Spinosa KernelOil Aristoflex Velvet 0.8 Polyacrylate Crosspolmer-11 Avocado oil 5 3Persea Gratissima (Avocado) Oil Beeswax 3 Cera Alba Belsil DMC 6038 2PEG 15-Methyl Ether Dimethicone Black currant oil 3 Ribes Nigrum (BlackCurrant) Seed Oil Borage oil 5 Borago Officinalis Seed Oil Brazilian nutoil 0.5 Bertholletia Excelsa Seed Oil Buriti oil 0.2 0.1 MauritiaFlexuosa Fruit Oil Carbopol Ultrez 10 0.25 0.6 Carbomer Castor Oil 8Ricinus Communis (Castor) Seed Oil Citric acid 10% solution 0.25 0.150.1 Citric acid Cocamidopropyl Betaine 38% 5 Cocamidopropyl BetaineCocoa butter 1 Theobroma Cacao (Cocoa) Seed Butter CI 12.490 (sol. 0.5%)0.27 CI 12490 CI 14.720 (sol. 0.5%) 0.07 CI 14720 CI 19.140 (sol. 0.5%)0.3 0.03 CI 19140 CI 42.090 (sol. 0.5%) 0.02 CI 42090 COSMETIC COLOURBLACK 14 C.I. 77492, 77499 Crinipan AD 0.3 Climbazole Cupuaçu butter 2Theobroma Grandiflorum Seed Butter Cutina FS 45 1 Stearic Acid, PalmiticAcid DC 245 Fluid 10 4 Cyclopentasiloxane DC 345 Fluid 0.2Cyclomethicone Diammonium Citrate 0.1 Diammonium Citrate Dimethicone 0.5Dimethicone Dissodium EDTA 0.1 0.1 0.1 Dissodium EDTA Dracorin 100 SEP 7Glyceryl Stearate, PEG-100 Stearate Dracorin GMS 2 4 2.5 6 Glycerylstearate Dragoderm 0.5 Glycerin, Triticum Vulgare Gluten, AquaDragosantol 0.2 0.1 0.05 Bisabolol, Farnesol Dragoxat 89 3 6 4 5Ethylhexyl Isononanoate Dry Flo Pure 3 Aluminum Starch OctenylsuccinateEmulsiphos 2 3 1.3 Potassium Cetyl Phosphate, Hydrogenated PalmGlycerides Eumulgin B2 2.5 6 Ceteareth-20 Eutanol G 8 OctyldodecanolEvening primrose oil 5 Oenothera Biennis (Evening Primrose) OilExtrapone Nutgrass (Motha) 0.5 Root GW Water (Aqua), Glycerin, CyperusRotundus Root extr. Fragrance 0.2 0.5 8 0.3 0.1 1 Perfum FrescolatX-Cool 0.1 Menthyl Ethylamido Oxalate Glycerin 15 0.5 3 3 2 5 GlycerinGrape seed oil 10 1.5 Vitis Vinifera (Grape) Seed Oil Hydrolite 5 3 2 5Pentylene Glycol Isodragol 3 Triisononanoin Isopropyl Myristate 0.5Isopropyl Myristate Isopropyl Palmitate 3 Isopropyl Palmitate Jojoba oil0.5 1.5 Simmondsia Chinensis (Jojoba) Seed Oil Lanette 16 1 4 2 1 CetylAlcohol Lanette O 3.6 3.5 2.5 Cetearyl Alcohol Marlinat 242/90 M 15 MIPALaureth Sulfate, Propylene Glycol Marlowet CG 2 PEG-18 Castor OilDioleate Medium Mineral Oil Ad 100 Paraffinum Liquidum Mineral oil 2Paraffinum Liquidum Mulsifan CPA 10 Laureth-4 Murumuru butter 2Astrocaryum Murumuru Seed Butter Neo Heliopan BB 0.5 Benzophenone-3Neutral oil 25 Caprylic/capric triglyceride Olive oil Ad 100 0.5 OleaEuropaea (Olive) Fruit Oil Oxynex ® ST Liquid 0.3 DiethylhexylSyringylidene Malonate, Caprylic/Capric Triglyceride Panthenol 0.5Panthenol Paracera M 2 Cera Microcrystalina PCL Liquid 100 1 CetearylEthylhexanoate PCL Solid 1 Stearyl Heptanoate, Stearyl Caprylate Perfumeoil PFO1 2 0.3 Perfume oil PFO2 0.6 Phytoconcentrole Arnica 1 GlycineSoja (Soybean) Oil, Arnica Montana Flower Extract PhytoconcentroleCamomile 3 Glycine Soja (Soybean) Oil, Bisabolol, Chamomilla Recutita(Matricaria) Flower Extract Plantacare 1200 UP 0.5 Lauryl GlucosidePluronic L-31 3 Poloxamer 101 Polyglyceryl-5 Oleate 6 Polyglyceryl-5Oleate Polyquaternium-10 0.3 Polyquaternium-10 Propylene Glycol 12Propylene Glycol PVP-K 30 Powder 3 PVP Reach 501 15 AluminiumChlorhydrate Retinol SU 10 0.2 Glycine Soja (Soybean) Oil, Retinol Sheabutter 1 2 0.1 Butyrospermum Parkii (Shea) Butter Sodium Chloride 1.5Sodium Chloride Sodium Hydroxide (sol. 30%) q.s. q.s. 0.05 SodiumHydroxide Solubilizer 0.5 PEG-40 Hydrogenated Castor Oil, Trideceth-9,Propylene Glycol, Water (Aqua) Soybean oil Ad Glycine Soja (Soybean) Oil100 Super Hartolan 0.2 Lanolin Alcohol Sweet almond oil 2 PrunusAmygdalus Dulcis (Sweet Almond) Oil SymCalmin 1 Butylene Glycol,Pentylene Glycol, Hydroxyphenyl Propamidobenzoic Acid SymDiol 68 0.8Caprylyl Glycol, 1,2- Hexanediol SymHair Force 1631 0.5 PentyleneGlycol, Isochrysis Galbana Extract SymMollient S 1 Cetearyl NonanoateSymOcide PS 0.8 0.5 Phenoxyethanol, Decylene Glycol, 1,2-HexanediolSymPeptide 226EL 2 Water (Aqua), Glycerin, Myristoyl Pentapeptide-17SymRelief 100 0.2 Bisabolol, Zingiber Officinalis (Ginger) Root ExtractSymTriol 0.8 Caprylyl Glycol, 1,2- Hexanediol, Methylbenzyl AlcoholSymWhite 377 0.5 Phenylethyl Resorcinol Tagat L2 2.5 PEG-20 GlycerylLaurate Tocopheryl acetate 0.3 Tocopheryl acetate Triethanolamine 99%0.7 Triethanolamine Tween 20 0.5 Polysorbate 20 Vaseline 3 PetrolatumWater App. 1.43 Add 100 Ad 100 Ad 100 Ad 100 Ad 100 Ad 100 Ad 100 Ad 100Aqua Xanthan gum 0.5 0.25 0.2 Xanthan gum Zetesol 100 43 MIPA-LaurethSulfate, Laureth-4, Cocamide DEA

Composition of perfume oils PFO1 and PFO2 (DPG=dipropylene glycol) aregiven in Tables 11 and 12.

TABLE 11 Perfume oil PFO1 Component/Name Parts b.w. Acetophenone, 10% inDPG 10.00 n-Undecanal 5.00 Aldehyde C14, so-called (peach aldehyde)15.00 Allylamyl glycolate, 10% in DPG 20.00 Amyl salicylate 25.00 Benzylacetate 60.00 Citronellol 80.00 d-Limonene 50.00 Decenol trans-9 15.00Dihydromyrcenol 50.00 Dimethylbenzylcarbinyl acetate 30.00 Diphenyloxide5.00 Eucalyptol 10.00 Geraniol 40.00 Nerol 20.00 Geranium oil 15.00Hexenol cis-3, 10% in DPG 5.00 Hexenyl salicylate cis-3 20.00 Indole,10% in DPG 10.00 Alpha-ionone 15.00 Beta-ionone 5.00 Lilial ®(2-methyl-3-(4-tert-butyl-phenyl)propanal) 60.00 Linalool 40.00Methylphenyl acetate 10.00 Phenylethyl alcohol 275.00 Styrolyl acetate20.00 Terpineol 30.00 Tetrahydrolinalool 50.00 Cinnamyl alcohol 10.00Total: 1,000.00

TABLE 12 Perfume oil PFO2 Component/Name Parts b.w. Benzyl acetate 60.00Citronellyl acetate 60.00 Cyclamenaldehyde(2-methyl-3-(4-isopropylphenyl)propanal 20.00 Dipropylene glycol (DPG)60.00 Ethyllinalool 40.00 Florol(2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol) 30.00 Globanone ®[(E/Z)-8-cyclohexadecen-1-one] 180.00 Hedione ® (methyldihydrojasmonate)140.00 Hexenyl salicylate, cis-3 10.00 Vertocitral(2,4-dimethyl-3-cyclohexenecarboxaldehyde) 5.00 Hydratropaaldehyde, 10%in DPG 5.00 Isodamascone (1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-5.00 1-one, 10% in DPG Isomuscone (cyclohexadecanone) 40.00 Jacinthaflor(2-methyl-4-phenyl-1,3-dioxolane) 10.00 Cis-jasmone, 10% in DPG 20.00Linalool 50.00 Linalyl acetate 30.00 Methyl benzoate, 10% in DPG 25.00para-Methyl cresol, 10% in DPG 10.00 Nerol 20.00 Phenylpropylaldehyde5.00 2-Phenylethyl alcohol 82.00 Tetrahydrogeraniol 13.002,2-Dimethyl-3-cyclohexyl-1-propanol 80.00 Total: 1,000.00

Example 6 Gelatine Capsules for Direct Consumption

TABLE 13 Gelatine capsule for direct consumption WEIGHT % RAW MATERIALNAME I II III IV Gelatine shell: Glycerin 2.014 2.014 2.014 2.014Gelatine 240 Bloom 7.91 7.91 7.91 7.91 Sucralose 0.065 0.065 0.065 0.065Allura Red 0.001 0.006 \ \ Brillant Blue \ 0.005 \ 0.005 Corecomposition: Borage oil \ \ Ad 100 \ Evening primrose oil Ad 100 \ \ \Wheat germ oil \ Ad 100 \ \ Salmon oil \ \ \ Ad 100 Aroma \ 12.0 1.0 \4-Hydroxyacetophenone 0.1 0.05 0.05 0.1

Aroma used in the gelatine capsule had the following composition (in wt.%): 0.1% neotame powder, 0.05% aspartame, 29.3% peppermint oil arvensis,29.3% peppermint piperita oil Willamette, 2.97% sucralose, 2.28%triacetin, 5.4% diethyl tartrate, 12.1% peppermint oil yakima, 0.7%ethanol, 3.36% 2-hydroxyethyl menthyl carbonate, 3.0% 2-hydroxypropylmenthyl carbonate, 0.27% vanillin, 5.5% D-limonene, 5.67% L-menthylacetate.

The gelatine capsule suitable for direct consumption (produced in ananalogous way to WO 2004/050069) had a diameter of 5 mm and the weightratio of core material to shell material was 90:10. The capsule openedin the mouth in less than 10 seconds and dissolved completely in lessthan 50 seconds.

Example 7 Flavoured Vegetable Oils for Culinary Use

TABLE 14 Flavoured vegetable oils for culinary use WEIGHT % RAW MATERIALNAME I II III IV Basil extract 0.3 \ 0.1 \ Corn oil \ \ Ad 100 \ Chiliextract \ 0.1 \ \ Lemon flavor \ \ \ 1   Olive oil \ \ 30   \4-Hydroxyacetophenone  0.05 0.2 0.1 0.1 Pumpkin seed oil \ 5   \ \Rapeseed oil \ \ \ Ad 100 Soybean oil \ Ad 100\ \ \ Sunflower oil Ad 10050   \ \ Tomato flavor \ \ 0.5 \ Walnut oil 3   \ \ \

These vegetable oils can be used to flavour various kinds of warm orcold dishes.

1. A composition with stabilized taste and/or odor, comprising (a) atleast one acetophenone derivative of formula (I)

wherein R₁ stands for hydrogen or methyl, and R₂ stands for hydrogen,hydroxyl or an —OCH₃ group, or a cosmetically or pharmaceuticallyacceptable salt thereof, and (b) at least one mono- or polyunsaturatedC₈-C₂₂ fatty acid or its monohydric or polyhydric C₁-C₁₈ aliphaticalcohol ester.
 2. The composition of claim 1, wherein the acetophenonederivative of formula (I) is selected from the group consisting of

and mixtures thereof.
 3. The composition of claim 1, wherein thecomponent (b) comprises (b-1) at least one acyl compound of formula (II)

wherein R stands for hydrogen atom or a C₁-C₁₈ alkyl group, and Xrepresents a mono- or polyunsaturated C₈-C₂₂ acyl group, and/or (b-2) atleast one acylglycerol compound of formula (III)

wherein X′, X″ and X″′ independently of one another represents ahydrogen atom or a saturated or mono- or polyunsaturated C₈-C₂₂ acylgroup, with the proviso that X′, X″ and X″′ do not simultaneouslyrepresent a hydrogen atom and at least one of X′, X″ and X″′ being anunsaturated acyl group.
 4. The composition of claim 3, wherein incomponent (b-1), R is a hydrogen atom and X is a mono- orpolyunsaturated C₁₆-C₂₂ acyl group.
 5. The composition of claim 4,wherein component (b-1) is selected from the group consisting of oleicacid, linoleic acid, γ-linolenic acid, α-linolenic acid, EPA and DHA andmixtures thereof.
 6. The composition of claim 3, wherein component (b-2)is selected from the group consisting of oleic, linoleic, and linolenicesterified on a glycerol molecule and mixtures thereof.
 7. Thecomposition of claim 1, comprising component (a) in an amount from 0.01to 5 wt. %, based on the total weight of the composition.
 8. A cosmeticcomposition comprising the composition of claim
 1. 9. A food compositioncomprising the composition of claim
 1. 10. A method for stabilizing thetaste and/or odor of mono- or polyunsaturated C₈-C₂₂ fatty acid or itsmonohydric or polyhydric C₁-C₁₈ aliphatic alcohol ester, comprisingadding an acetophenone derivative of formula (I)

wherein R₁ stands for hydrogen or methyl, and R₂ stands for hydrogen,hydroxyl or an —OCH₃ group, or a cosmetically or pharmaceuticallyacceptable salt thereof to said mono- or polyunsaturated C₈-C₂₂ fattyacid or its monohydric or polyhydric C₁-C₁₈ aliphatic alcohol ester. 11.The method of claim 10, wherein the acetophenone derivative of formula(I) is selected from the group consisting of

and mixtures thereof.
 12. The method of claim 10, wherein the mono- orpolyunsaturated C₈-C₂₂ fatty acid or its monohydric or polyhydric C₁-C₁₈alkyl alcohol ester comprises (b-1) at least one acyl compound offormula (II)

wherein R stands for hydrogen atom or an C₁-C₁₈ alkyl group, and Xrepresents a mono- or polyunsaturated C₈-C₂₂ acyl group, and/or (b-2) atleast one acylglycerol compound of formula (III)

wherein X′, X″ and X″′ independently of one another represents ahydrogen atom or a saturated or mono- or polyunsaturated C₈-C₂₂ acylgroup, with the proviso that X′, X″ and X″′ do not simultaneouslyrepresent a hydrogen atom and at least one of X′, X″ and X″′ being anunsaturated acyl group.
 13. The method of claim 10, wherein the addedamount of acetophenone derivative of formula (I) is from 0.01 to 5 wt.%, based on the total weight.
 14. A method for stabilizing the tasteand/or odor of unsaturated fatty acids (esters), comprising adding anacetophenone derivative of formula (I)

wherein R₁ stands for hydrogen or methyl, and R₂ stands for hydrogen,hydroxyl or an —OCH₃ group, or a cosmetically or pharmaceuticallyacceptable salt thereof into said unsaturated fatty acid (esters). 15.The method of claim 14, wherein the added amount of acetophenonederivative of formula (I) is from 0.01 to 5 wt. %, based on the totalweight.